CN116162017A - Preparation method of trans-resveratrol - Google Patents

Preparation method of trans-resveratrol Download PDF

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CN116162017A
CN116162017A CN202310107153.5A CN202310107153A CN116162017A CN 116162017 A CN116162017 A CN 116162017A CN 202310107153 A CN202310107153 A CN 202310107153A CN 116162017 A CN116162017 A CN 116162017A
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resveratrol
organic solvent
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reaction
halogenated
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蒋其柏
安珂
荀燕鹏
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Shaanxi Yuanheng Pharmaceutical Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
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    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract

The invention belongs to the technical field of resveratrol preparation, and particularly relates to a preparation method of trans-resveratrol, which comprises the following steps: s1, dissolving tribenzyloxy resveratrol in an organic solvent A in a hydrogen atmosphere, and purifying by hydrogenation reaction under the action of a catalyst to obtain dihydro resveratrol; s2, under the atmosphere of protective gas, dissolving the dihydro-resveratrol prepared in the step S1 and a halogenated reagent in an organic solvent B, and preparing a halogenated intermediate I crude product through halogenated reaction; s3, under the atmosphere of protective gas, dissolving the halogenated intermediate I crude product prepared in the S2 in an organic solvent C, carrying out dehalogenation olefination reaction with alkali, and purifying to obtain a product trans-resveratrol; the preparation method has the advantages of multiple sources of raw materials, obvious cost advantage, more convenience, environmental protection, high total yield, less three wastes and higher purity, and is beneficial to industrialization.

Description

Preparation method of trans-resveratrol
Technical Field
The invention belongs to the technical field of resveratrol preparation, and particularly relates to a preparation method of trans-resveratrol.
Background
Resveratrol (resveratrol) was found as early as 1924, and was found in vitis plants in 1974 and was first characterized as a substance that itself produced stress resistance. It is widely used in various plants and has important biological activities such as anti-tumor, antiviral, etc. At present, resveratrol plant extracts are prepared into capsules with the effects of regulating blood fat and resisting cancer.
The preparation of resveratrol has two methods, namely a plant extraction method and a synthesis method, the plant extraction method is abandoned gradually due to the problem of environmental pollution caused by the use of a large amount of a class-A solvent, and the organic synthesis method is studied greatly, wherein in the methods, different groups are usually adopted to protect hydroxyl groups, such as methyl, benzyl and the like, but Lewis acids such as aluminum trichloride, boron tribromide and the like are usually introduced in the deprotection process, so that a large amount of three wastes are generated, and the treatment cost is greatly increased.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method of trans-resveratrol.
The invention is realized by the following technical scheme.
A preparation method of trans-resveratrol comprises the following steps:
s1, dissolving tribenzyloxy resveratrol in an organic solvent A in a hydrogen atmosphere, carrying out hydrogenation reaction under the action of a catalyst, and purifying to obtain dihydro resveratrol;
s2, under the atmosphere of protective gas, dissolving the dihydro-resveratrol prepared in the S1 and a halogenating reagent in an organic solvent B to carry out halogenation reaction, and purifying to prepare a halogenated intermediate I crude product;
s3, under the atmosphere of protective gas, dissolving the halogenated intermediate I crude product prepared in the S2 in an organic solvent C, carrying out dehalogenation olefination reaction with alkali, and purifying to obtain a product trans-resveratrol;
the synthetic route is as follows:
Figure BDA0004075509230000021
preferably, in S1, the catalyst is any one or two of palladium carbon, raney nickel, ruthenium carbon and rhodium carbon, and the molar ratio of the tribenzyloxy resveratrol to the catalyst is 100:1-10.
Preferably, in S1, the hydrogen pressure is 0.1-5MPa.
Preferably, in S2, the halogenated reagent is NBS, bromine, hydrogen peroxide and hydrobromic acid, NCS, NIS, I 2 、Cl 2 Any one or two of cyanuric chloride, dibromohydantoin and dichlorohydantoin, and the mol ratio of the dihydroresveratrol to the halogenated reagent is 1:1-5.
Preferably, in S3, the base is any one or two of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium hydride, sodium methoxide, sodium tert-butoxide and potassium tert-butoxide, and the molar ratio of the halogenated intermediate I to the base is 1:1-5.
Preferably, the organic solvent A, the organic solvent B and the organic solvent C are any one of halogenated hydrocarbon solvents, aromatic solvents, ether solvents, ester solvents or alcohol solvents and strong polar solvents containing hetero atoms respectively;
the molar ratio of the organic solvent A to the tribenzyloxy resveratrol is 1-10:1; the mol ratio of the organic solvent B to the dihydro-resveratrol is 1-10:1; the molar ratio of the organic solvent C to the halogenated intermediate I is 1-10:1.
More preferably, the halogenated hydrocarbon solvent comprises dichloromethane and dichloroethane; the aromatic solvent comprises toluene and xylene; the ether solvent comprises tetrahydrofuran; the ester solvent comprises methyl acetate and ethyl acetate; the alcohol solvent comprises methanol, ethanol and glycol; the strong polar solvent containing hetero atoms includes DMF, DMA, DMSO, NMP, sulfolane and DMI.
Preferably, the reaction temperatures in S1 and S2 are respectively 0-100 ℃; in S3, the reaction temperature is-50-150 ℃.
More preferably, the reaction temperature in S1 and S2 is 50-80 ℃ respectively; in S3, the reaction temperature is-30-10 ℃.
Compared with the prior art, the invention has the following beneficial effects:
in order to solve the problems of a large amount of waste water generated in the process of synthesizing trans-resveratrol by using Lewis acid in the prior art, a new synthetic route is provided, and in particular, the trans-resveratrol is obtained by three steps of reaction of hydrogenation, halogenation and olefination by taking tribenzyloxy resveratrol as a raw material in an organic solvent at a certain temperature, the raw material sources are more, the cost advantage is obvious, the use of Lewis acid is avoided in the preparation process, the preparation method is more convenient and environment-friendly, the total yield is high, the three wastes are less, the purity is higher, and the industrialization is facilitated.
Detailed Description
In order that those skilled in the art will better understand the technical scheme of the present invention, the present invention will be further described with reference to specific examples and data, but the examples are not intended to limit the present invention.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available unless otherwise specified.
The invention provides a preparation method of trans-resveratrol, which comprises the following steps:
s1, dissolving tribenzyloxy resveratrol in an organic solvent A in a hydrogen atmosphere, carrying out hydrogenation reaction under the action of a catalyst, and purifying to obtain dihydro resveratrol;
s2, under the atmosphere of protective gas, dissolving the dihydro-resveratrol prepared in the S1 and a halogenating reagent in an organic solvent B to carry out halogenation reaction, and purifying to prepare a halogenated intermediate I crude product;
s3, under the atmosphere of protective gas, dissolving the halogenated intermediate I crude product prepared in the S2 in an organic solvent C, carrying out dehalogenation olefination reaction with alkali, and purifying to obtain a product trans-resveratrol;
the synthetic route is as follows:
Figure BDA0004075509230000041
wherein the organic solvent A, the organic solvent B and the organic solvent C are any one of halogenated hydrocarbon solvents, aromatic solvents, ether solvents, ester solvents or alcohol solvents and strong polar solvents containing hetero atoms respectively; the halogenated hydrocarbon solvent comprises dichloromethane and dichloroethane; the aromatic solvent comprises toluene and xylene; the ether solvent comprises tetrahydrofuran; the ester solvent comprises methyl acetate and ethyl acetate; the alcohol solvent comprises methanol, ethanol and glycol; the strong polar solvent containing hetero atoms includes DMF, DMA, DMSO, NMP, sulfolane and DMI. The alkali is any one or two of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium hydride, sodium methoxide, sodium tert-butoxide and potassium tert-butoxide. The halogenated reagent is NBS, bromine, hydrogen peroxide and hydrobromic acid, NCS, NIS, I 2 、Cl 2 Any one or two of cyanuric chloride, dibromohydantoin and dichlorohydantoin. The catalyst A is any one or two of palladium carbon, raney nickel, ruthenium carbon and rhodium carbon.
The above is specifically described below by way of the following examples.
Firstly, the dihydro resveratrol is synthesized firstly, and the synthesis equation is as follows:
Figure BDA0004075509230000051
the above synthesis is specifically illustrated by the following examples.
Example 1
49.8g (0.10 mol) of tribenzyloxy resveratrol, 100mL of methanol and 1g of 3% ruthenium-carbon solid are put into a 500mL high-pressure reaction kettle, the pressure is set to be 1MPa after nitrogen is replaced three times and hydrogen is replaced three times, the mixture is heated to 50 ℃ for stirring reaction for 12 hours, the temperature and the pressure are reduced, after a catalyst is recovered by filter pressing, the methanol is recovered by normal-pressure distillation (directly applied to the next batch reaction), the recovery rate is 90%, 50mL of water is added, ethyl acetate is extracted and desolventized to obtain >98% dihydro resveratrol, the weight of a product is 20.7g, and the yield is 90%.
Example 2
49.8g (0.10 mol) of tribenzyloxy resveratrol, 100mL of methanol and 1g of 5% palladium carbon solid are put into a 500mL high-pressure reaction kettle, the pressure is set to be 1MPa after nitrogen is replaced three times and hydrogen is replaced three times, the mixture is heated to 50 ℃ for stirring reaction for 12 hours, the temperature and the pressure are reduced, after the catalyst is recovered by filter pressing, the methanol is recovered by normal-pressure distillation (directly applied to the next batch reaction), the recovery rate is 90%, 50mL of water is added, ethyl acetate is extracted and desolventized to obtain >98% of dihydro resveratrol, the product weight is 21.85g, and the yield is 95%.
Example 3
49.8g (0.10 mol) of tribenzyloxy resveratrol, 100mL of methanol and 1g of Raney nickel are put into a 500mL high-pressure reaction kettle, the pressure is set to be 1MPa after nitrogen replacement and hydrogen replacement are carried out three times, the mixture is heated to 50 ℃ and stirred for reaction for 12 hours, the temperature and the pressure are reduced, the pressure is relieved, after the catalyst is recovered by filter pressing, the methanol is recovered by normal-pressure distillation (directly being applied to the next batch of reaction), the recovery rate is 90 percent, 50mL of water is added, ethyl acetate is used for extraction and desolventizing to obtain the dihydro resveratrol with the concentration of more than 98 percent, the weight of the product is 18.86g, and the yield is 82 percent.
Example 4
49.8g (0.10 mol) of tribenzyloxy resveratrol, 100mL of methanol and 1g of 1% rhodium-carbon solid are put into a 500mL high-pressure reaction kettle, the pressure is set to be 1MPa after nitrogen is replaced three times and hydrogen is replaced three times, the mixture is heated to 50 ℃ for stirring reaction for 12 hours, the temperature and the pressure are reduced, after a catalyst is recovered by filter pressing, the methanol is recovered by normal-pressure distillation (directly applied to the next batch reaction), the recovery rate is 90%, 50mL of water is added, ethyl acetate is extracted and desolventized to obtain >98% of dihydro resveratrol, the product weight is 20.24g, and the yield is 88%.
Example 5
Adding 49.8g k g of tribenzyloxy resveratrol, 200L of methanol and 100g of 5% palladium-carbon solid of a catalyst into a 500L high-pressure reaction kettle, setting the pressure to 2MPa after nitrogen replacement and hydrogen replacement for three times, heating to 50 ℃ for stirring reaction for 12h, cooling and pressure relief, and carrying out normal-pressure distillation to recover methanol (directly applying to the next batch reaction) after pressure filtration to recover the catalyst, wherein the recovery rate is 93%, adding 100L of water, and extracting and desolventizing 200L of ethyl acetate to obtain the dihydro-resveratrol with the concentration of more than 98%.
According to the embodiment, the dihydro resveratrol is successfully synthesized by the step, the post treatment in the reaction process is simple, lewis acid is not used, the waste water production is small, and the method is suitable for industrial synthesis.
Second, halogenated intermediate I is synthesized, the synthesis equation is as follows:
Figure BDA0004075509230000071
the above synthesis is specifically illustrated by the following examples.
Example 6
Under the protection of nitrogen, 23g (0.10 mol) of dihydroresveratrol, 200mL of dichloroethane and 17.8g (0.1 mol) of NBS are put into a 500mL reaction kettle, the mixture is slowly heated to 50 ℃ for reaction for 24 hours under the heat preservation and stirring, the temperature is reduced to room temperature, brominated intermediate I and succinimide byproducts are obtained through filtration, 100mL of solid water is added for pulping to remove succinimide, so that a brominated intermediate I wet product is obtained, 27.7g of finished product is obtained through drying, and the yield is 89.5%; the filtered filtrate dichloroethane (directly used for the next reaction).
Example 7
Under the protection of nitrogen, 23g (0.10 mol) of dihydroresveratrol, 200mL of dichloroethane and 0.1mol of bromine are put into a 500mL reaction kettle, the mixture is slowly heated to 50 ℃ for heat preservation and stirring reaction for 24 hours, the temperature is reduced to room temperature, brominated intermediate I and succinimide byproducts are obtained by filtration, 100mL of water is added into the solid, and the succinimide is removed by pulping, so that a brominated intermediate I wet product is obtained, and the yield is 12%; the filtered filtrate dichloroethane (directly used for the next reaction).
Example 8
Under the protection of nitrogen, 23g (0.10 mol) of dihydroresveratrol, 200mL of dichloroethane and 0.1mol of hydrogen peroxide and hydrobromic acid are put into a 500mL reaction kettle, the mixture is slowly heated to 50 ℃ for heat preservation and stirring reaction for 24 hours, the temperature is reduced to room temperature, brominated intermediate I and succinimide byproducts are obtained by filtration, 100mL of solid is added with water, and the succinimide is removed by pulping, so that a brominated intermediate I wet product is obtained, and the yield is 28%; the filtered filtrate dichloroethane (directly used for the next reaction).
Example 9
Under the protection of nitrogen, 23g (0.10 mol) of dihydroresveratrol, 200mL of dichloroethane and 0.1mol of chlorine are put into a 500mL reaction kettle, the mixture is slowly heated to 50 ℃ for heat preservation and stirring reaction for 24 hours, the temperature is reduced to room temperature, brominated intermediate I and succinimide byproducts are obtained by filtration, 100mL of solid is added with water, and the succinimide is removed by beating, so that a brominated intermediate I wet product is obtained, and the yield is 65%; the filtered filtrate dichloroethane (directly used for the next reaction).
Example 10
Under the protection of nitrogen, 23g (0.10 mol) of dihydroresveratrol, 200mL of dichloroethane and 0.1mol of NCS are put into a 500mL reaction kettle, the mixture is slowly heated to 50 ℃ for heat preservation and stirring reaction for 24 hours, the temperature is reduced to room temperature, brominated intermediate I and succinimide byproducts are obtained by filtration, 100mL of solid is added with water, pulping is carried out, and the succinimide is removed to obtain a brominated intermediate I wet product, and the yield is 59%; the filtered filtrate dichloroethane (directly used for the next reaction).
Example 11
Under the protection of nitrogen, 23g (0.10 mol) of dihydroresveratrol, 200mL of dichloroethane and 0.1mol of NIS are put into a 500mL reaction kettle, the mixture is slowly heated to 50 ℃ for heat preservation and stirring reaction for 24 hours, the temperature is reduced to room temperature, brominated intermediate I and succinimide byproducts are obtained by filtration, 100mL of water is added into the solid, and the succinimide is removed by pulping, so that a brominated intermediate I wet product is obtained, and the yield is 74%; the filtered filtrate dichloroethane (directly used for the next reaction).
Example 12
Under the protection of nitrogen, 23g (0.10 mol) of dihydroresveratrol, 200mL of dichloroethane and I are put into a 500mL reaction kettle 2 0.1mol, slowly heating to 50 ℃, keeping the temperature, stirring and reacting for 24 hours, cooling to room temperature, filtering to obtain a brominated intermediate I and a succinimide byproduct, adding 100ml of water into the solid, pulping to remove the succinimide, and obtaining a brominated intermediate I wet product with a yield of 5%; the filtered filtrate dichloroethane (directly used for the next reaction).
As can be seen from the above examples, the present invention synthesizes the brominated intermediate I by changing the kind of the halogenated reagent, and has the advantages of simple synthetic route and strong operability.
Thirdly, synthesizing resveratrol, wherein the synthesis equation is as follows:
Figure BDA0004075509230000091
the above synthesis is specifically illustrated by the following examples.
Example 13
Under the protection of nitrogen, 30.8 g (0.10 mol) of bromointermediate I, 100mL of methanol and 100mL of water are put into a 500mL reaction kettle, 0.12mol (96 mL) of 5% sodium hydroxide solution is dropwise added at 0 ℃, the dropwise addition is completed, the heat preservation is carried out for 1h, 20g of resveratrol is obtained through suction filtration, water washing and drying, the yield is 87.7%, and the purity is 99.9%.
Therefore, the invention successfully synthesizes the resveratrol through simple olefination on the basis of the synthesized halogenated intermediate I, has simple synthesis process, strong operability and high purity of the synthesized product, and is suitable for industrial production and application.
It will be apparent to those skilled in the art that various modifications and variations can be made to the present invention without departing from the spirit or scope of the invention. Thus, it is intended that such modifications and variations be included herein within the scope of the appended claims and their equivalents.

Claims (9)

1. The preparation method of trans-resveratrol is characterized by comprising the following steps of:
s1, dissolving tribenzyloxy resveratrol in an organic solvent A in a hydrogen atmosphere, carrying out hydrogenation reaction under the action of a catalyst, and purifying to obtain dihydro resveratrol;
s2, under the atmosphere of protective gas, dissolving the dihydro-resveratrol prepared in the S1 and a halogenating reagent in an organic solvent B to carry out halogenation reaction, and purifying to prepare a halogenated intermediate I;
s3, under the atmosphere of protective gas, dissolving the halogenated intermediate I prepared in the S2 in an organic solvent C, carrying out dehalogenation olefination reaction with alkali, and purifying to obtain the product trans-resveratrol.
2. The preparation method of trans-resveratrol according to claim 1, wherein in S1, the catalyst is any one or two of palladium carbon, raney nickel, ruthenium carbon and rhodium carbon, and the molar ratio of the tribenzyloxy resveratrol to the catalyst is 100:1-10.
3. The method for preparing trans-resveratrol according to claim 1, wherein in S1, the hydrogen pressure is 0.1-5MPa.
4. The method for preparing trans-resveratrol according to claim 1, wherein in S2, the halogenated reagent is NBS, bromine, hydrogen peroxide+hydrobromic acid, NCS, NIS, I 2 、Cl 2 Any one of cyanuric chloride, dibromohydantoin and dichlorohydantoin, and the mol ratio of the dihydroresveratrol to the halogenated reagent is 1:1-5.
5. The method for preparing trans-resveratrol according to claim 1, wherein in S3, the base is any one or two of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium hydride, sodium methoxide, sodium tert-butoxide and potassium tert-butoxide, and the molar ratio of halogenated intermediate I to base is 1:1-5.
6. The method for preparing trans-resveratrol according to claim 1, wherein the organic solvent a, the organic solvent B and the organic solvent C are any one of halogenated hydrocarbon solvents, aromatic solvents, ether solvents, ester solvents or alcohol solvents, respectively, and polar solvents containing hetero atoms;
the molar ratio of the organic solvent A to the tribenzyloxy resveratrol is 1-10:1; the mol ratio of the organic solvent B to the dihydro-resveratrol is 1-10:1; the molar ratio of the organic solvent C to the halogenated intermediate I is 1-10:1.
7. The method for preparing trans-resveratrol according to claim 6, wherein the halogenated hydrocarbon solvent comprises dichloromethane and dichloroethane; the aromatic solvent comprises toluene and xylene; the ether solvent comprises tetrahydrofuran; the ester solvent comprises methyl acetate and ethyl acetate; the alcohol solvent comprises methanol, ethanol and glycol; the polar solvent containing hetero atoms includes DMF, DMA, DMSO, NMP, sulfolane and DMI.
8. The method for preparing trans-resveratrol according to claim 1, wherein the reaction temperatures in S1 and S2 are 0-100 ℃ respectively; in S3, the reaction temperature is-50-150 ℃.
9. The method for preparing trans-resveratrol according to claim 8, wherein the reaction temperatures in S1 and S2 are 50-80 ℃ respectively; in S3, the reaction temperature is-30-10 ℃.
CN202310107153.5A 2023-02-14 2023-02-14 Preparation method of trans-resveratrol Pending CN116162017A (en)

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