阅读说明：本技术 一种由2,4,6-三羟基苯乙酮制备短叶松素的方法 (Method for preparing pinobanksin from 2,4, 6-trihydroxyacetophenone ) 是由 柳刚 于 2020-06-17 设计创作，主要内容包括：本发明涉及一种由2,4,6-三羟基苯乙酮制备短叶松素的方法,该制备方法由醚化步骤(A)、苯甲醛加合步骤(B)、过氧化氢氧化步骤(C)与酸解步骤(D)按照其顺序组成。本发明制备方法使用原料易于得到,反应条件温和,副产物少,产率高达80％以上,产物纯度高达98.5％以上,整个制备过程对环境污染很小,本发明解决了人们一直都未解决的采用人工合成短叶松素的技术难题。(The invention relates to a method for preparing pinobanksin from 2,4, 6-trihydroxyacetophenone, which consists of an etherification step (A), a benzaldehyde addition step (B), a hydrogen peroxide oxidation step (C) and an acidolysis step (D) in sequence. The preparation method has the advantages of easily obtained used raw materials, mild reaction conditions, less by-products, high yield of more than 80 percent, high product purity of more than 98.5 percent and little environmental pollution in the whole preparation process, and solves the technical problem of adopting artificial synthesis of pinosylvin which is not solved all the time by people.)

1. A method for preparing pinobanksin from 2,4, 6-trihydroxyacetophenone is characterized in that the method for preparing the pinobanksin comprises an etherification step (A), a benzaldehyde addition step (B), a hydrogen peroxide oxidation step (C) and an acidolysis step (D) in sequence.

2. The pinobanksin production method according to claim 1, wherein the etherification step (a) is performed in the following manner:

under stirring, the molar ratio of 2,4, 6-trihydroxyacetophenone, NaH and DMF is 1: 4-5: 10-50, dissolving 2,4, 6-trihydroxyacetophenone and NaH in DMF, carrying out heating reflux in a heating reflux device at the temperature of 80-85 ℃, and then mixing the obtained solution according to the molar ratio of 2,4, 6-trihydroxyacetophenone to chloromethyl methyl ether of 1: 4-5, adding chloromethyl methyl ether, continuously heating and refluxing for 3-4 hours, finishing the reaction when the reaction solution turns turbid from clear, and detecting the compound of the chemical formula I and the 2,4, 6-trihydroxyacetophenone in the reaction solution by adopting a TLC method;

when no 2,4, 6-trihydroxyacetophenone was detected, the ratio of ice water to DMF was 1: 1-2, quenching by using ice water, continuously adding the ice water to separate out crystals of the compound of the chemical formula I, filtering and drying to obtain a product, namely the compound of the chemical formula I; the reaction equation is as follows:

3. the method according to claim 2, wherein chloromethyl methyl ether is replaced with bromomethyl methyl ether.

4. The method for producing pinobanksin according to claim 2, wherein the compound of formula I is crystallized by allowing to stand in ice water.

5. The pinobanksin preparation method according to claim 1, wherein the benzaldehyde addition step (B) is performed in the following manner:

the molar ratio of the compound of formula I to ethanol is 1: 10-50 adding the product of the compound of formula I prepared in the etherification step (A) to an ethanol solution, and then adding a catalyst in a molar ratio of the compound of formula I to KOH of 1: 4.2-4.8, adding KOH, and performing heating reflux for 0.5-1.0 hour in a heating reflux device at the temperature of 75-85 ℃, wherein the molar ratio of the compound shown in the formula I to benzaldehyde is 1: 0.8-1.2 adding benzaldehyde, continuously heating and refluxing for 3-6 hours, and detecting the compound of the chemical formula II and the compound of the chemical formula I in the reaction solution by adopting a TLC method;

when the compound of the chemical formula I is not detected, carrying out evaporation concentration, quenching by using a dilute hydrochloric acid solution, extracting by using an ethyl acetate extractant, and evaporating an extract phase to dryness to obtain a product, namely a compound of the chemical formula II; the reaction equation is as follows:

6. the method of producing pinobanksin according to claim 5, wherein the ratio of the volume of the quenching solution to the volume of the extractant in the range of 1: and repeatedly extracting for 2-4 times by using an ethyl acetate extractant under the condition of 1-3 times.

7. The pinobanksin production method according to claim 1, wherein the hydrogen peroxide oxidation step (C) is carried out in the following manner:

the molar ratio of the compound of formula II to methanol is 1: 10-50 dissolving the compound of formula II prepared in the step (B) of benzaldehyde addition in methanol, and then mixing the compound of formula II with NaOH according to a molar ratio of 1: 0.5-1.5 adding NaOH catalyst, heating and refluxing for 0.5-1.0H in a heating and refluxing device at 50-60 ℃, and then reacting the compound with H according to the chemical formula II₂O₂Mole ofThe ratio of 1: 0.8 to 1.2, and adding H with the concentration of 28 to 32 percent by volume₂O₂Continuously heating and refluxing the solution for 1-3 hours, detecting the compound of the chemical formula III in the reaction solution by adopting a TLC method, and then quenching by using a dilute hydrochloric acid solution; the reaction equation is as follows:

8. the method of claim 7, wherein the dilute hydrochloric acid solution is an aqueous hydrochloric acid solution having a concentration of 0.5-2.0N.

9. The process for producing pinobanksin according to claim 1, wherein the acid hydrolysis step (D) is carried out in the following manner:

adjusting the pH value of the quenching solution obtained in the step (C) by hydrogen peroxide oxidation to 2-3 by using a hydrochloric acid solution, carrying out heating reflux for 2-4 hours in a heating reflux device at the temperature of 55-70 ℃, detecting the compound of the chemical formula IV in the reaction solution by using a TLC (thin layer chromatography) method, extracting by using an ethyl acetate extractant, and evaporating an extract phase to dryness to obtain the compound of the chemical formula IV; the reaction equation is as follows:

10. the process for producing pinobanksin according to claim 9, wherein the volume ratio of the reaction solution to the extractant in the reaction solution is 1: and repeatedly extracting for 2-4 times by using an ethyl acetate extractant under the condition of 1-3 times.

[ technical field ] A method for producing a semiconductor device

The invention belongs to the technical field of compound synthesis. More particularly, the present invention relates to a method for preparing pinobanksin from 2,4, 6-trihydroxyacetophenone.

[ background of the invention ]

Propolis contains abundant bioactive components such as flavonoids, has abundant pharmacological activity, and contains pinobanksin and its derivatives with effects of strengthening blood vessel, resisting bacteria, resisting inflammation, resisting oxidation, preventing liver function injury, and protecting liver. Therefore, the scientists in China have conducted extensive research on the extraction, separation and content determination of pinobanksin in propolis, for example, Wenling et al have studied the process and content determination method for extracting and preparing pinobanksin from propolis in the subject "extraction, separation and content determination of pinobanksin in propolis," practical combined clinical practice of Chinese and Western medicine ", 17(1), p155-157 (2017"). CN 104592188A discloses a method for separating and purifying pinobanksin and caffeic acid derivatives from Chinese propolis aqueous extract, which comprises the steps of preparing Chinese propolis aqueous extract; precipitating with ethanol; coarse separation with macroporous adsorption resin; separating and purifying by semi-preparative high performance liquid chromatography to obtain pinobanksin, etc.

However, no patent application or other literature reports on the preparation of pinobanksin by chemical synthesis have been found.

[ summary of the invention ]

[ problem to be solved ]

The invention aims to provide a method for preparing pinobanksin from 2,4, 6-trihydroxyacetophenone.

[ solution ]

The invention is realized by the following technical scheme.

The invention relates to a method for preparing pinobanksin from 2,4, 6-trihydroxyacetophenone.

The preparation method of the pinobanksin comprises an etherification step (A), a benzaldehyde addition step (B), a hydrogen peroxide oxidation step (C) and an acidolysis step (D) in sequence.

According to a preferred embodiment of the invention, the etherification step (a) is carried out in the following manner:

under stirring, the molar ratio of 2,4, 6-trihydroxyacetophenone, NaH and DMF is 1: 4-5: 10-50, dissolving 2,4, 6-trihydroxyacetophenone and NaH in DMF, carrying out heating reflux in a heating reflux device at the temperature of 80-85 ℃, and then mixing the obtained solution according to the molar ratio of 2,4, 6-trihydroxyacetophenone to chloromethyl methyl ether of 1: 4-5, adding chloromethyl methyl ether, continuously heating and refluxing for 3-4 hours, finishing the reaction when the reaction solution turns turbid from clear, and detecting the compound of the chemical formula I and the 2,4, 6-trihydroxyacetophenone in the reaction solution by adopting a TLC method:

when the 2,4, 6-trihydroxyacetophenone is not detected, quenching by using ice water according to the volume ratio of the ice water to the DMF (dimethyl formamide) of 1: 1-2, continuously adding the ice water to separate out crystals of the compound of the chemical formula I, filtering and drying to obtain the compound of the chemical formula I; the reaction equation is as follows:

according to another preferred embodiment of the invention, chloromethyl methyl ether is replaced by bromomethyl methyl ether.

According to another preferred embodiment of the present invention, the compound of formula I is crystallized under standing conditions in ice water.

According to another preferred embodiment of the present invention, the benzaldehyde addition step (B) is carried out in the following manner:

the molar ratio of the compound of formula I to ethanol is 1: 10-50 adding the product of the compound of formula I prepared in the etherification step (A) to an ethanol solution, and then adding a catalyst in a molar ratio of the compound of formula I to KOH of 1: 4.2-4.8, adding KOH, and performing heating reflux for 0.5-1.0 hour in a heating reflux device at the temperature of 75-85 ℃, wherein the molar ratio of the compound shown in the formula I to benzaldehyde is 1: 0.8-1.2 adding benzaldehyde, continuously heating and refluxing for 3-6 hours, and detecting the compound of the chemical formula II and the compound of the chemical formula I in the reaction solution by adopting a TLC method;

when the compound of the chemical formula I is not detected, carrying out evaporation concentration, quenching by using a dilute hydrochloric acid solution, extracting by using an ethyl acetate extractant, and evaporating an extract phase to dryness to obtain a product, namely a compound of the chemical formula II; the reaction equation is as follows:

according to another preferred embodiment of the present invention, a separatory funnel extraction apparatus is used to separate the quench solution from the extractant in a volume ratio of 1: and repeatedly extracting for 2-4 times by using an ethyl acetate extractant under the condition of 1-3 times.

According to another preferred embodiment of the present invention, the hydrogen peroxide oxidation step (C) is carried out in the following manner:

the molar ratio of the compound of formula II to methanol is 1: 10-50 dissolving the compound of formula II prepared in the step (B) of benzaldehyde addition in methanol, and then mixing the compound of formula II with NaOH according to a molar ratio of 1: 0.5-1.5 adding NaOH catalyst, heating and refluxing for 0.5-1.0H in a heating and refluxing device at 50-60 ℃, and then reacting the compound with H according to the chemical formula II₂O₂1: 0.8 to 1.2, and adding H with the concentration of 28 to 32 percent by volume₂O₂Heating and refluxing the solution for 1-3 hours, and detecting by adopting a TLC methodMeasuring the compound of formula III in the reaction solution, and then quenching with a dilute hydrochloric acid solution; the reaction equation is as follows:

according to another preferred embodiment of the present invention, the dilute hydrochloric acid solution is a 0.5-2.0N hydrochloric acid aqueous solution.

According to another preferred embodiment of the invention, the acidolysis step (D) is carried out in the following way:

adjusting the pH value of the quenching solution obtained in the step (C) by hydrogen peroxide oxidation to 2-3 by using a hydrochloric acid solution, carrying out heating reflux for 2-4 hours in a heating reflux device at the temperature of 55-70 ℃, detecting the compound of the chemical formula IV in the reaction solution by using a TLC (thin layer chromatography) method, extracting by using an ethyl acetate extractant, and evaporating an extract phase to dryness to obtain the compound of the chemical formula IV; the reaction equation is as follows:

according to another preferred embodiment of the present invention, a separatory funnel extraction apparatus is used to separate the reaction solution and the extractant in a volume ratio of 1: and repeatedly extracting for 2-4 times by using an ethyl acetate extractant under the condition of 1-3 times.

The present invention will be described in more detail below.

The invention relates to a method for preparing pinobanksin from 2,4, 6-trihydroxyacetophenone.

The preparation method of the pinobanksin comprises an etherification step (A), a benzaldehyde addition step (B), a hydrogen peroxide oxidation step (C) and an acidolysis step (D) in sequence.

These steps will be specifically described below, respectively.

In the etherification step (a), the following etherification reactions are carried out:

specifically, the etherification step (a) is carried out in the following manner:

under stirring, the mixture was stirred according to a molar ratio of 2,4, 6-trihydroxyacetophenone, NaH to DMF (dimethylformamide) of 1: 4-5: 10-50, dissolving 2,4, 6-trihydroxyacetophenone and NaH in DMF, carrying out heating reflux in a heating reflux device at the temperature of 80-85 ℃, and then mixing the obtained solution according to the molar ratio of 2,4, 6-trihydroxyacetophenone to chloromethyl methyl ether of 1: and 4-5, adding chloromethyl methyl ether, continuously heating and refluxing for 3-4 hours, finishing the reaction when the reaction solution turns turbid from clear, and detecting the compound of the chemical formula I and the 2,4, 6-trihydroxyacetophenone in the reaction solution by adopting a TLC (thin layer chromatography) method:

and when the 2,4, 6-trihydroxyacetophenone is not detected, quenching by using ice water according to the volume ratio of the ice water to the DMF (dimethyl formamide) of 1: 1-2, continuously adding the ice water to separate out crystals of the compound of the chemical formula I, filtering and drying to obtain the compound of the chemical formula I.

In the present invention, the molar ratio of 2,4, 6-trihydroxyacetophenone, NaH and DMF (dimethylformamide) is 1: 4-5: 10 to 50. If the amount of NaH is less than 4, the reaction lasts too long; if the use amount of NaH is more than 5, catalyst waste is caused, and the difficulty of later purification is increased; therefore, the use amount of NaH is suitably 4 to 5; if the dosage of DMF is less than 10, the solid reagent can not be ensured to be completely dissolved, the reaction rate is reduced, and the yield is reduced; if the amount of DMF is more than 50, the reaction time is prolonged due to too low concentration of the reaction solution; therefore, the amount of DMF is preferably 10 to 50. Thus, the molar ratio of 2,4, 6-trihydroxyacetophenone, NaH and DMF (dimethylformamide) is preferably 1: 4.2-4.8: 18-42, more preferably 1: 4.4-4.6: 25 to 35.

Of course, other organic solvents may be used in the present invention, provided that they do not adversely affect the etherification reaction and subsequent reactions, and such organic solvents are within the scope of the present invention.

The molar ratio of the 2,4, 6-trihydroxyacetophenone to chloromethyl methyl ether is 1: 4 to 5. If the amount of chloromethyl methyl ether used is less than 4, this leads to incomplete reaction and to prolonged reaction times; if the dosage of chloromethyl methyl ether is higher than 5, the purification difficulty is increased; therefore, the amount of chloromethyl methyl ether is 4-5, preferably 4.2-4.8, and more preferably 4.4-4.6.

In the present invention, the heating reflux temperature is very critical, if the heating temperature is lower than 80 ℃, the temperature is too low to reduce the reaction rate; if the heating temperature is higher than 85 ℃, unnecessary energy waste is caused; therefore, the heating temperature is reasonable to be 80-85 ℃; likewise, the heating reflux time is also very important, and if the heating reflux time is shorter than 3 hours, the reaction is not complete; if the heating reflux time is longer than 4 hours, the energy waste and the generation of byproducts are caused; therefore, the heating reflux time is preferably 3 to 4 hours.

The starting materials used in the present invention, such as 2,4, 6-trihydroxyacetophenone and chloromethyl methyl ether, are commercially available products, for example, 2,4, 6-trihydroxyacetophenone which is sold under the trade name of 2,4, 6-trihydroxyacetophenone by Hansa chemical Co., Ltd., Shanghai, chloromethyl methyl ether which is sold under the trade name of chloromethyl methyl ether by sigmaaldrich, Ltd.

The heating reflow apparatus used in the present invention is a product generally used in the prior art and sold on the market at present, for example, a heating reflow apparatus sold under the trade name crown sub heating cycle apparatus by Wuxi crown sub constant temperature refrigeration technology Co.

Thin Layer Chromatography (TLC) is a detection method that rapidly separates and qualitatively analyzes small amounts of substances. In the present invention, the thin layer chromatograph used is a product sold under the trade name thin layer chromatograph by Hencokadskyo technologies, Beijing. The conditions for thin layer chromatography are conventional analytical conditions effective to distinguish between the starting material and the product developing reagent. Methods for identifying chemical products are conventional¹The HNMR identification method can adopt the detection condition of a deuterated reagent of chloroform or dimethyl sulfoxide. The following thermal refluxing apparatus, Thin Layer Chromatography (TLC) and¹the HNMR identification method is the same, and therefore, the description is omitted.

According to the invention, the chloromethyl methyl ether used in this step can be replaced by bromomethyl methyl ether, the other conditions remaining unchanged.

In the present invention, when 2,4, 6-trihydroxyacetophenone was not detected by TLC method, the ratio of ice water to DMF was 1: 1-2 quenching with ice water. And (3) precipitating the compound of the chemical formula I in ice water under the condition of standing.

The crystals of the compound of formula I obtained by filtration are dried in an infrared drying oven drying apparatus under heating until the water content thereof reaches less than 1% by weight.

The crystalline product obtained in this step was confirmed by examination according to the method described in the specification of the present application to be a compound of formula I, and the yield in this step was 95% or more by mass.

In the benzaldehyde addition step (B), the following benzaldehyde addition reaction is carried out:

specifically, the benzaldehyde addition step (B) is carried out in the following manner:

the molar ratio of the compound of formula I to ethanol is 1: 10-50 adding the product of the compound of formula I prepared in the etherification step (A) to an ethanol solution, and then adding a catalyst in a molar ratio of the compound of formula I to KOH of 1: 4.2-4.8, adding KOH, and performing heating reflux for 0.5-1.0 hour in a heating reflux device at the temperature of 75-85 ℃, wherein the molar ratio of the compound shown in the formula I to benzaldehyde is 1: 0.8-1.2 adding benzaldehyde, continuously heating and refluxing for 3-6 hours, and detecting the compound of the chemical formula II and the compound of the chemical formula I in the reaction solution by adopting a TLC method;

in the present invention, if the molar ratio of the compound of formula I to ethanol is greater than 1: 10, the solid reagent can not be completely dissolved, the reaction rate is reduced, and the yield is reduced; if the molar ratio of the compound of formula I to ethanol is less than 1: 50, the reaction time is prolonged due to the excessively low concentration of the reaction solution; thus, the molar ratio of the compound of formula I to ethanol is 1: 10 to 50 is reasonable, preferably 1: 18-42, more preferably 1: 25 to 36.

If the molar ratio of the compound of formula I to KOH is greater than 1: 4.2, prolonging the reaction time; if the molar ratio of the compound of formula I to KOH is less than 1: 4.8, the waste of the catalyst is caused, and the difficulty of later purification is increased; thus, the molar ratio of the compound of formula I to KOH is 1: 4.2 to 4.8 are suitable, preferably 1: 4.4 to 4.6;

if the molar ratio of the compound of formula I to benzaldehyde is greater than 1: 0.8, the reaction is incomplete; if the molar ratio of the compound of formula I to benzaldehyde is less than 1: 1.2, the reaction is incomplete; thus, the molar ratio of the compound of formula I to benzaldehyde is 1: 0.8 to 1.2 is appropriate;

in this step, heating the reflux temperature and time beyond the above-mentioned range is not preferable because the reaction rate is lowered due to too low temperature or short time, resulting in incomplete reaction. Too high temperature or too long time causes energy waste and byproducts.

Evaporating and concentrating when the compound of the chemical formula I is not detected by adopting a TLC method, quenching by using a dilute hydrochloric acid solution, extracting by using an ethyl acetate extractant, and evaporating an extract phase to dryness to obtain a product, namely a compound of the chemical formula II;

in this step, the evaporative concentration apparatus used is a product currently marketed, for example, by Shanghai virtud laboratory instruments Co., Ltd. under the trade name of a rotary evaporator.

Evaporating and concentrating to be liquid-free by using an evaporation and concentration device under the reduced pressure distillation condition.

The dilute hydrochloric acid solution used for quenching the evaporated and concentrated solution is a hydrochloric acid aqueous solution with the concentration of 0.5-2.0N.

According to the invention, a separating funnel extraction device is used to extract the quench solution to the extractant in a volume ratio of 1: and repeatedly extracting for 2-4 times by using an ethyl acetate extractant under the condition of 1-3 times.

The conditions for evaporating the extract phase to dryness were as follows: evaporating and concentrating to be liquid-free by using an evaporation and concentration device under the reduced pressure distillation condition.

The detection according to the method described in the specification of the application confirms that the product obtained in this step is a compound of formula II, and the yield in this step is 90% or more by mass.

In the hydrogen peroxide oxidation step (C), the following hydrogen peroxide oxidation reaction is carried out:

specifically, the hydrogen peroxide oxidation step (C) is carried out in the following manner:

the molar ratio of the compound of formula II to methanol is 1: 10-50 dissolving the compound of formula II prepared in the step (B) of benzaldehyde addition in methanol, and then mixing the compound of formula II with NaOH according to a molar ratio of 1: 0.5-1.5 adding NaOH catalyst, heating and refluxing for 0.5-1.0H in a heating and refluxing device at 50-60 ℃, and then reacting the compound with H according to the chemical formula II₂O₂1: 0.8 to 1.2, and adding H with the concentration of 28 to 32 percent by volume₂O₂Continuously heating and refluxing the solution for 1-3 hours, detecting the compound of the chemical formula III in the reaction solution by adopting a TLC method, and then quenching by using a dilute hydrochloric acid solution;

in this step, if the molar ratio of the compound of formula II to methanol is greater than 1: 10, the complete dissolution of the solid reagent cannot be ensured, the reaction rate is reduced, and the yield is reduced; if the molar ratio of the compound of formula II to methanol is less than 1: 50, the reaction time is prolonged due to the fact that the concentration of the reaction liquid is too low; thus, the molar ratio of the compound of formula II to methanol is 1: 10 to 50 is reasonable, preferably 1: 20-40, more preferably 1: 26 to 34.

If the molar ratio of the compound of formula II to NaOH is greater than 1: 0.5, prolonging the reaction time; if the molar ratio of the compound of formula II to NaOH is less than 1: 1.5, the waste of the catalyst is caused, and the difficulty of later purification is increased; thus, the molar ratio of the compound of formula II to NaOH is 1: 0.5 to 1.5 is feasible, preferably 1: 0.8 to 1.2.

If the compound of the formula II is reacted with H₂O₂Is greater than 1: 0.8, the rate of incomplete reaction is reduced; if changeCompounds of formula II and H₂O₂Is less than 1: 1.2, the incomplete reaction rate is reduced; thus, compounds of formula II with H₂O₂In a molar ratio of 1: 0.8 to 1.2 is suitable, preferably 1: 0.9 to 1.1.

In this step, when the NaOH catalyst is added, it is not preferable to heat the reflux temperature and time beyond the above-mentioned range because the reaction rate is lowered due to too low temperature or short time, resulting in incomplete reaction. Too high temperature or too long time causes energy waste and byproducts. Addition of H₂O₂When the solution is heated at reflux for a time exceeding the above range, it is also not suitable because the reaction rate is lowered due to too low temperature or short time, resulting in incomplete reaction. Too high temperature or too long time causes energy waste and byproducts.

According to the invention, the dilute hydrochloric acid solution used for quenching is a hydrochloric acid aqueous solution with the concentration of 0.5-2.0N.

The detection according to the method described in the specification of the application confirms that the product obtained in this step is a compound of formula III, and the yield in this step is 70% or more by mass.

In the acidolysis step (D), the following acidolysis reaction is carried out:

specifically, the acidolysis step (D) is carried out in the following manner:

adjusting the pH value of the quenching solution obtained in the step (C) by using a hydrochloric acid solution to 2-3, carrying out heating reflux for 2-4 hours in a heating reflux device at the temperature of 55-70 ℃, detecting the compound of the chemical formula IV in the reaction solution by using a TLC method, extracting by using an ethyl acetate extractant, and evaporating an extract phase to dryness to obtain the compound of the chemical formula IV, namely pinobanksin:

and (3) adjusting the pH of the quenching solution obtained in the step (C) by oxidizing hydrogen peroxide to 2-3 by using a hydrochloric acid solution. The main purpose of adjusting the pH of the quenching solution is to neutralize sodium hydroxide, providing an electron donating group;

in this step, it is not preferable that the heating reflux temperature and the heating reflux time exceed the above-mentioned ranges because the reaction rate is lowered due to too low temperature or short time, resulting in incomplete reaction. Too high temperature or too long time causes energy waste and byproducts.

According to the invention, a separating funnel extraction device is used to extract the reaction solution and the extractant at a volume ratio of 1: and repeatedly extracting for 2-4 times by using an ethyl acetate extractant under the condition of 1-3 times.

The conditions for evaporating the extract phase to dryness were as follows: evaporating and concentrating to be liquid-free by using an evaporation and concentration device under the reduced pressure distillation condition.

The detection according to the method described in the specification of the application confirms that the product obtained in this step is the compound of formula IV, and the yield in this step is 80% or more by mass.

According to the calculation of a mass formula, the yield of the pinobanksin prepared by the preparation method is over 80 percent.

By Thin Layer Chromatography (TLC) with¹The purity of the pinosylvin of the product prepared by the preparation method is over 98.5 percent by HNMR method detection.

[ advantageous effects ]

The invention has the beneficial effects that: the preparation method has the advantages of easily obtained used raw materials, mild reaction conditions, less by-products, high yield of more than 80 percent, high product purity of more than 98.5 percent and little environmental pollution in the whole preparation process, and solves the technical problem of adopting artificial synthesis of pinosylvin which is not solved all the time by people.

[ detailed description ] embodiments

The invention will be better understood from the following examples.