CN113735693A - Synthesis method of resveratrol monomethyl ether - Google Patents
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- C—CHEMISTRY; METALLURGY
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Abstract
The invention provides a synthesis method of resveratrol dimethyl ether, which comprises the following steps: A) mixing resveratrol, a solvent and a phase transfer catalyst to obtain an initial mixture; B) and (3) reacting the initial mixture with a methylating agent in an alkaline environment, and purifying to obtain the resveratrol trimethyl ether. The synthesis method provided by the application takes resveratrol as an initial raw material, obtains resveratrol trimethyl ether through one-step methylation reaction, and has the advantages of simple synthesis process, mild conditions, yield of more than 98.5%, good quality and content of more than 99.5%. The method for synthesizing the resveratrol trimethyl ether provided by the invention saves the cost and is easy for industrial production.
Description
Technical Field
The invention relates to the technical field of pharmaceutical chemistry synthesis, in particular to a synthesis method of resveratrol monomethyl ether.
Background
Resveratrol trimethyl ether is a trimethylated derivative of resveratrol, has anti-inflammatory effect similar to resveratrol, and can improve the condition of osteoarthritis; it has obvious effects of resisting neovascularization and mitosis, and also has the effects of resisting allergy, protecting gastric mucosa from damage and resisting aging; it can more remarkably cause microtubule decomposition and tubulin depolymerization, and can be used as anti-tumor medicine.
Resveratrol trimethyl ether can also be used as an important synthetic raw material of a plurality of antibacterial drugs, antiobesity drugs, anticancer drugs and auxiliary agents, such as H-PGDS inhibitors, Rho-kinase inhibitors, KSP inhibitors, CSF-1R inhibitors, renin inhibitors and the like with anticancer effects. Therefore, the development of a method for synthesizing resveratrol trimethyl ether has practical significance.
Different processes are available for synthesizing resveratrol monomethyl ether, and at present, two main process routes are available: 1) p-methoxybenzyl bromide reacts with triphenylphosphine to generate p-methoxybenzyl triphenyl phosphonium bromide, then the p-methoxybenzyl triphenyl phosphonium bromide reacts with 3, 5-dimethoxybenzaldehyde through Wittig to generate racemic isomeric trimethoxy stilbene, and finally trans-3, 4' -oxy stilbene resveratrol monomethyl ether is obtained through methods such as column chromatography and the like; 2) 3, 5-dimethoxy benzyl bromide reacts with triethyl phosphite to generate 3, 5-dimethoxy benzyl diethyl phosphonate, and then the 3, 5-dimethoxy benzyl diethyl phosphonate reacts with p-methoxybenzaldehyde through Wittig-Horner reaction to prepare trans-resveratrol monomethyl ether. The method has the defects of complex process, harsh reaction conditions, large harm of used raw materials to the environment, low yield and high cost.
Disclosure of Invention
The invention aims to provide a synthesis method of resveratrol dimethyl ether, which has the advantages of simple process, mild conditions and high yield.
In view of the above, the present application provides a method for synthesizing resveratrol monomethyl ether, comprising the following steps:
A) mixing resveratrol, a solvent and a phase transfer catalyst to obtain an initial mixture;
B) and (3) reacting the initial mixture with a methylating agent in an alkaline environment, and purifying to obtain the resveratrol trimethyl ether.
Preferably, the phase transfer catalyst is selected from quaternary ammonium salts selected from benzyltriethylammonium chloride, benzyltrimethylammonium chloride or hexadecyltributylammonium bromide; the phase transfer catalyst is 0.1-0.5 wt% of the resveratrol.
Preferably, the alkaline environment is pH 11-12.
Preferably, the methylating agent is selected from dimethyl sulphate or dimethyl carbonate.
Preferably, the process of obtaining the initial mixture is specifically:
mixing resveratrol and a solvent under a protective atmosphere, adding a phase transfer catalyst, and stirring for 20-30 min; the solvent is an ethanol water solution with the concentration of 10-20 wt%.
Preferably, the reaction process is specifically as follows:
dropwise adding an alkaline solution and a methylating agent into the initial mixture, controlling the pH of the system to 11-12, reacting until the residual amount of resveratrol is less than or equal to 0.1%, and finally adding an acid solution to neutralize the pH to 5-6.
Preferably, the dropping temperature is 30-40 ℃, and the time is 20-50 min; the reaction temperature is 30-40 ℃, and the reaction time is 2-5 h.
Preferably, the alkaline solution is a sodium hydroxide solution, and the acid solution is dilute sulfuric acid.
Preferably, the purification step specifically comprises:
starting a vacuum device for the system after reaction, keeping the vacuum degree of-0.095 to-0.097 Mpa, controlling the water bath temperature to be 40-45 ℃, carrying out reduced pressure distillation, stopping reduced pressure distillation when the distillation gas phase temperature reaches 40 ℃ at most, and closing the vacuum; and (3) rapidly cooling to 15-20 ℃ with cold water, keeping the temperature at 15-20 ℃, stirring for 45-60 min, then filtering, leaching a filter cake with purified water, compacting, pumping, and drying at 35-40 ℃ for 5-6 h under vacuum.
The application provides a synthesis method of resveratrol dimethyl ether, which comprises the following steps: firstly, mixing resveratrol, a solvent and a phase transfer catalyst to obtain an initial mixture; and reacting the initial mixture with a methylating agent in an alkaline environment, and purifying to obtain the resveratrol trimethyl ether. The resveratrol trimethyl ether is obtained by taking resveratrol as an initial raw material through one-step methylation reaction, the synthesis process is simple, the synthesis process conditions are mild, the yield is over 98.5%, the quality is good, and the content is more than 99.5%.
Drawings
FIG. 1 is a graph of the data for the detection of resveratrol monomethyl ether prepared in example 1.
Detailed Description
For a further understanding of the invention, reference will now be made to the preferred embodiments of the invention by way of example, and it is to be understood that the description is intended to further illustrate features and advantages of the invention, and not to limit the scope of the claims.
The synthesis of the resveratrol by converting the glucose through enzyme in a cell factory is realized, and the scale production is formed; the resveratrol trimethyl ether is obtained by taking the resveratrol which is easily obtained in the market as an initial raw material through one-step methylation, the synthesis process is simple, the yield is high and is more than 98.5%, the quality is good, and the content is more than 99.5%. Specifically, the embodiment of the invention discloses a method for synthesizing resveratrol dimethyl ether, which comprises the following steps:
A) mixing resveratrol, a solvent and a phase transfer catalyst to obtain an initial mixture;
B) and (3) reacting the initial mixture with a methylating agent in an alkaline environment, and purifying to obtain the resveratrol trimethyl ether.
In the process of obtaining the initial mixture, the solvent is selected from ethanol, specifically 10-20% ethanol water solution, and the mass ratio of the resveratrol to the ethanol water solution is 1: (3-5), more specifically, the mass ratio of the resveratrol to the ethanol aqueous solution is 1: (4-4.5). The phase transfer catalyst is selected from quaternary ammonium salts, more specifically, the phase transfer catalyst is selected from one or more of benzyltriethylammonium chloride, benzyltrimethylammonium chloride and hexadecyltributylammonium bromide; the phase transfer catalyst is 0.1-0.5 wt% of the resveratrol, and more specifically, the phase transfer catalyst is 0.2-0.4 wt% of the resveratrol. The resveratrol may be synthesized according to a method well known to those skilled in the art, and the present application is not particularly limited.
On the basis of fully mixing the raw materials, dropwise adding alkali liquor and a methylating agent, reacting, and purifying to obtain the resveratrol trimethyl ether. In this process, the methylating agent is selected from dimethyl sulphate or dimethyl carbonate; the molar ratio of the methylation reagent to the resveratrol is (3-4): 1, more specifically, the molar ratio of the methylating agent to the resveratrol is (3.45-3.75): 1. in the process, the pH value of the reaction system is kept between 11 and 12, more specifically between 11 and 11.5, and the alkaline environment is favorable for the reaction. The reaction process is as follows:
dropwise adding an alkaline solution and a methylating agent into the initial mixture, controlling the pH of the system to 11-12, reacting until the residual amount of resveratrol is less than or equal to 0.1%, and finally adding an acid solution to neutralize the pH to 5-6.
In the process, the dropping temperature is 30-40 ℃, and the time is 20-50 min; the reaction temperature is 30-40 ℃, and the reaction time is 2-5 h; more specifically, the dropping temperature is 30-35 ℃, the time is 30-40 min, the reaction time is 30-35 ℃, and the reaction time is 3.5 h. The alkaline solution is sodium hydroxide solution, and the acid solution is dilute sulfuric acid.
The method is finally purified to obtain the resveratrol dimethyl ether with high purity; the purification steps are specifically as follows:
starting a vacuum device for the system after reaction, keeping the vacuum degree of-0.095 to-0.097 Mpa, controlling the water bath temperature to be 40-45 ℃, carrying out reduced pressure distillation, stopping reduced pressure distillation when the distillation gas phase temperature reaches 40 ℃ at most, and closing the vacuum; and (3) rapidly cooling to 15-20 ℃ with cold water, keeping the temperature at 15-20 ℃, stirring for 45-60 min, then filtering, leaching a filter cake with purified water, compacting, pumping, and drying at 35-40 ℃ for 5-6 h under vacuum.
The reaction formula for synthesizing resveratrol monomethyl ether specifically comprises:
aiming at the problems of complex synthesis process, multiple used chemical raw materials and low yield and high cost of the prior resveratrol trimethyl ether, the method takes the resveratrol which is easily obtained in the market as the initial raw material, obtains the resveratrol trimethyl ether through one-step methylation reaction, and has the advantages of simple synthesis process, mild synthesis process conditions, high yield of over 98.5 percent, good quality and content of more than 99.5 percent.
For further understanding of the present invention, the following examples are provided to illustrate the synthesis of resveratrol monomethyl ether provided by the present invention, and the scope of the present invention is not limited by the following examples.
Example 1
Under the protection of nitrogen, 22.8g of resveratrol is added into a 250ml flask, then 92g of 15% ethanol aqueous solution is added, 50mg of hexadecyl tributyl ammonium bromide serving as a catalyst is added, and stirring is carried out for 25 min; then simultaneously dropwise adding 30% sodium hydroxide solution and 45.81 dimethyl sulfate, controlling the dropwise adding temperature to be 30-35 ℃, keeping the pH value of a reaction system to be 11-11.3 in the dropwise adding process, keeping the temperature to be 30-35 ℃ for continuously reacting for 3.5h after dropwise adding is finished, sampling, carrying out controlled detection, keeping the residual amount of resveratrol to be 0.09%, and then adding 20% dilute sulfuric acid into the system to neutralize the pH value of the system to be 5.5; starting vacuum, keeping the vacuum degree between-0.095 and-0.097 Mpa, setting the water bath temperature at 40-45 ℃, distilling ethanol water under reduced pressure, stopping reduced pressure distillation when the temperature of the distilled gas phase reaches 40 ℃ at most, and closing the vacuum; rapidly cooling to 15-20 ℃ with cold water, keeping the temperature of 15-20 ℃, stirring for 45min, then filtering, leaching a filter cake with purified water, compacting, pumping to obtain a wet resveratrol trimethyl ether product, and drying at 35-40 ℃ for 5.5h under vacuum to obtain 26.76g of a resveratrol trimethyl ether product shown in the specification, wherein the yield is 98.91%, and the HPLC content is 99.8%.
Through detection, the melting point of the prepared resveratrol dimethyl ether is 55-59 ℃;
nuclear magnetic resonance (H-NMR) characterization using a 400 million NMR spectrometer (BRUKER, Switzerland) model ADVANCE2B/400 MHZ; the detection results are shown in fig. 1, and the data are:1H NMR(DMSO-d6) 3.77(s,9H),6.39(s,1H),6.74(s,2H),6.94(d,2H, J ═ 8.4Hz),7.02(d,1H, J ═ 16.4Hz),7.21(d,1H, J ═ 16.4Hz),7.53(d,2H, J ═ 8.4 Hz). Therefore, the method can prove that the resveratrol dimethyl ether is obtained.
Example 2
Under the protection of nitrogen, 22.8g of resveratrol is added into a 250ml flask, then 97g of 15% ethanol aqueous solution is added, 92mg of benzyltrimethylammonium chloride serving as a catalyst is added, and stirring is carried out for 30 min; then, dropwise adding 43.98g of 30% sodium hydroxide solution and 43.98g of dimethyl sulfate at the same time, controlling the dropwise adding temperature to be 30-35 ℃, keeping the pH value of a reaction system to be 11-11.5 in the dropwise adding process, keeping the temperature to be 30-35 ℃ to continue reacting for 4 hours after dropwise adding is finished, sampling, carrying out controlled detection, keeping the residual amount of resveratrol to be 0.085%, and then adding 20% of dilute sulfuric acid into the system to neutralize the pH value of the system to be 5.7; starting vacuum, keeping the vacuum degree between-0.095 and-0.097 Mpa, setting the water bath temperature at 40-45 ℃, distilling ethanol water under reduced pressure, stopping reduced pressure distillation when the temperature of the distilled gas phase reaches 40 ℃ at most, and closing the vacuum; rapidly cooling to 15-20 ℃ with cold water, keeping the temperature of 15-20 ℃, stirring for 50min, then filtering, leaching a filter cake with purified water, compacting, pumping to obtain a wet resveratrol trimethyl ether product, and drying at 35-40 ℃ for 5.5h under vacuum to obtain 26.75g of a resveratrol trimethyl ether product, wherein the yield is 98.68% and the HPLC content is 99.6%.
Example 3
Under the protection of nitrogen, 22.8g of resveratrol is added into a 250ml flask, then 92g of 15% ethanol aqueous solution is added, 70mg of hexadecyl tributyl ammonium bromide serving as a catalyst is added, and stirring is carried out for 25 min; then simultaneously dropwise adding 46.59g of 30% sodium hydroxide solution and dimethyl sulfate, controlling the dropwise adding temperature to be 30-35 ℃, keeping the pH value of a reaction system to be 11-11.5 in the dropwise adding process, keeping the temperature to be 30-35 ℃ for continuously reacting for 3.0h after dropwise adding is finished, sampling, carrying out controlled detection, keeping the residual content of resveratrol to be 0.08%, and then adding 20% dilute sulfuric acid into the system to neutralize the pH value of the system to be 5.7; starting vacuum, keeping the vacuum degree between-0.095 and-0.097 Mpa, setting the water bath temperature at 40-45 ℃, distilling ethanol water under reduced pressure, stopping reduced pressure distillation when the temperature of the distilled gas phase reaches 40 ℃ at most, and closing the vacuum; rapidly cooling to 15-20 ℃ with cold water, keeping the temperature of 15-20 ℃, stirring for 45min, then filtering, leaching a filter cake with purified water, compacting, pumping to obtain a wet resveratrol trimethyl ether product, and drying at 35-40 ℃ for 5.5h under vacuum to obtain 26.77g of a resveratrol trimethyl ether product, wherein the yield is 98.85%, and the HPLC content is 99.7%.
Comparative example 1
Under the protection of nitrogen, 22.8g of resveratrol is added into a 250ml flask, then 92g of 15% ethanol aqueous solution is added, 50mg of hexadecyl tributyl ammonium bromide serving as a catalyst is added, and stirring is carried out for 25 min; then simultaneously dropwise adding 30% sodium hydroxide solution and 45.81 dimethyl sulfate, controlling the dropwise adding temperature to be 20-25 ℃, keeping the pH value of a reaction system to be 11-11.3 in the dropwise adding process, keeping the temperature to be 30-35 ℃ for continuously reacting for 3.5h after dropwise adding is finished, sampling, carrying out controlled detection, keeping the residual content of resveratrol to be 0.5%, and then adding 20% dilute sulfuric acid into the system to neutralize the pH value of the system to be 5.5; starting vacuum, keeping the vacuum degree between-0.095 and-0.097 Mpa, setting the water bath temperature at 40-45 ℃, distilling ethanol water under reduced pressure, stopping reduced pressure distillation when the temperature of the distilled gas phase reaches 40 ℃ at most, and closing the vacuum; rapidly cooling to 15-20 ℃ with cold water, keeping the temperature of 15-20 ℃, stirring for 45min, then filtering, leaching a filter cake with purified water, compacting, pumping to obtain a wet resveratrol trimethyl ether product, and drying for 5.5h at 35-40 ℃ under vacuum to obtain 26.49g of a resveratrol trimethyl ether product, wherein the yield is 97.23%, and the HPLC content is 99.1%.
Comparative example 2
Under the protection of nitrogen, 22.8g of resveratrol is added into a 250ml flask, then 92g of 15% ethanol aqueous solution is added, 50mg of hexadecyl tributyl ammonium bromide serving as a catalyst is added, and stirring is carried out for 25 min; then simultaneously dropwise adding 30% sodium hydroxide solution and 45.81 dimethyl sulfate, controlling the dropwise adding temperature to be 30-35 ℃, keeping the pH value of a reaction system to be 10-10.5 in the dropwise adding process, keeping the temperature to be 30-35 ℃ for continuously reacting for 3.5h after dropwise adding is finished, sampling, carrying out controlled detection, keeping the residual content of resveratrol to be 0.8%, and then adding 20% dilute sulfuric acid into the system to neutralize the pH value of the system to be 5.5; starting vacuum, keeping the vacuum degree between-0.095 and-0.097 Mpa, setting the water bath temperature at 40-45 ℃, distilling ethanol water under reduced pressure, stopping reduced pressure distillation when the temperature of the distilled gas phase reaches 40 ℃ at most, and closing the vacuum; rapidly cooling to 15-20 ℃ with cold water, keeping the temperature of 15-20 ℃, stirring for 45min, then filtering, leaching a filter cake with purified water, compacting, pumping to obtain a wet resveratrol trimethyl ether product, and drying for 5.5h at 35-40 ℃ under vacuum to obtain 26.43g of a resveratrol trimethyl ether product, wherein the yield is 96.91% and the HPLC content is 99.0%.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (9)
1. A synthesis method of resveratrol dimethyl ether comprises the following steps:
A) mixing resveratrol, a solvent and a phase transfer catalyst to obtain an initial mixture;
B) and (3) reacting the initial mixture with a methylating agent in an alkaline environment, and purifying to obtain the resveratrol trimethyl ether.
2. The synthesis method according to claim 1, wherein the phase transfer catalyst is selected from quaternary ammonium salts selected from benzyltriethylammonium chloride, benzyltrimethylammonium chloride or hexadecyltributylammonium bromide; the phase transfer catalyst is 0.1-0.5 wt% of the resveratrol.
3. The method of claim 1, wherein the alkaline environment is at a pH of 11 to 12.
4. The method of synthesis according to claim 1, wherein the methylating agent is selected from dimethyl sulfate or dimethyl carbonate.
5. The synthesis method according to claim 1, characterized in that the process of obtaining the initial mixture is in particular:
mixing resveratrol and a solvent under a protective atmosphere, adding a phase transfer catalyst, and stirring for 20-30 min; the solvent is an ethanol water solution with the concentration of 10-20 wt%.
6. The synthesis method according to claim 1, wherein the reaction process is specifically:
dropwise adding an alkaline solution and a methylating agent into the initial mixture, controlling the pH of the system to 11-12, reacting until the residual amount of resveratrol is less than or equal to 0.1%, and finally adding an acid solution to neutralize the pH to 5-6.
7. The synthesis method according to claim 6, wherein the dropping temperature is 30-40 ℃ and the time is 20-50 min; the reaction temperature is 30-40 ℃, and the reaction time is 2-5 h.
8. The synthesis method according to claim 6, wherein the alkaline solution is sodium hydroxide solution and the acid solution is dilute sulfuric acid.
9. The synthesis method according to claim 1, characterized in that the purification steps are in particular:
starting a vacuum device for the system after reaction, keeping the vacuum degree of-0.095 to-0.097 Mpa, controlling the water bath temperature to be 40-45 ℃, carrying out reduced pressure distillation, stopping reduced pressure distillation when the distillation gas phase temperature reaches 40 ℃ at most, and closing the vacuum; and (3) rapidly cooling to 15-20 ℃ with cold water, keeping the temperature at 15-20 ℃, stirring for 45-60 min, then filtering, leaching a filter cake with purified water, compacting, pumping, and drying at 35-40 ℃ for 5-6 h under vacuum.
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