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Highly-efficient synthetic method for 2, 6-dimethoxy-4-vinylphenol

A technology of vinylphenol and dimethoxy, which is applied in the field of efficient synthesis of 2,6-dimethoxy-4-vinylphenol, can solve the problems of low economy and low synthesis efficiency, and achieve catalytic effect Good, protection of biological activity, easy to operate

Inactive Publication Date: 2015-04-08
INST OF OIL CROPS RES CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the content of 2,6-dimethoxy-4-vinylphenol in oil is significantly increased after rapeseed is heat-treated, there are two problems in extracting and purifying this substance from oil: one is not economical Sex (the overall content is low), and the second is not necessary (it can improve the oxidation stability of oil in oil)
[0012] In summary, there is no patented technology for efficient synthesis of 2,6-dimethoxy-4-vinylphenol at home and abroad, although there are foreign literature reports on microwave synthesis methods using syringaldehyde and sinapic acid as raw materials, and 4-Acetoxy-3,5-dimethoxystyrene is a raw material hydrolysis synthesis method, but the synthesis efficiency is not high, so an efficient and simple 2,6-dimethoxy-4-vinyl The synthesis method of phenol has become one of the research hotspots

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0041] A kind of efficient synthetic method of 2,6-dimethoxyl-4-vinylphenol, comprises the steps:

[0042] (1) Preparation of solid phase reaction system: Weigh 1mmol sinapinic acid in a 20mL round bottom flask, add 2mL methanol to dissolve, then add 6mmol DBU, 0.1mmol hydroquinone and 1g alumina; connect the round bottom flask to a rotary evaporator instrument, set the temperature of the water bath to 40°C and the degree of vacuum to -0.05MPa, and remove the methanol in the reaction system by distillation under reduced pressure;

[0043] (2) Microwave synthesis: place the round bottom flask in a microwave oven, set the microwave power to 800W, and the microwave time to 20min, take out the flask after the reaction and cool to room temperature;

[0044] (3) Neutralization: add hydrochloric acid solution with a concentration of 1M, oscillate to fully contact the hydrochloric acid and DBU to neutralize the system until the system is neutral, and use pH test paper to detect;

[0...

Embodiment 2

[0050] A kind of efficient synthetic method of 2,6-dimethoxyl-4-vinylphenol, comprises the steps:

[0051] (1) Preparation of solid phase reaction system: Weigh 0.2mmol sinapinic acid in a 100mL round bottom flask, add 2mL methanol to dissolve, then add 1.2mmol DBU, 0.02mmol phenothiazine and 4mmol alumina; connect the round bottom flask to a rotating Evaporator, set the temperature of the water bath to 40°C, the degree of vacuum to -0.08MPa, and remove the methanol in the reaction system by distillation under reduced pressure;

[0052] (2) Microwave synthesis: place the round bottom flask in a microwave oven, set the microwave power to 800W, and the microwave time to 5min, take out the flask after the reaction and cool to room temperature;

[0053] (3) Neutralization: add hydrochloric acid solution with a concentration of 1M, oscillate to fully contact the hydrochloric acid and DBU to neutralize the system until the system is neutral, and use pH test paper to detect;

[0054...

Embodiment 3

[0059] A kind of efficient synthetic method of 2,6-dimethoxyl-4-vinylphenol, comprises the steps:

[0060] (1) Preparation of solid phase reaction system: Weigh 0.2mmol sinapinic acid in a 100mL round bottom flask, add 2mL methanol to dissolve, then add 1.8mmolDBN, 0.06mmol hydroquinone and 6mmol alumina; connect the round bottom flask to Rotary evaporator, set the temperature of the water bath to 35°C, the degree of vacuum to -0.06MPa, and remove the methanol in the reaction system by distillation under reduced pressure;

[0061] (2) Microwave synthesis: place the round bottom flask in a microwave oven, set the microwave power to 1200W, and the microwave time to 10min, take out the flask after the reaction and cool to room temperature;

[0062] (3) Neutralization: add hydrochloric acid solution with a concentration of 1.5M, oscillate to fully contact the hydrochloric acid and DBU to neutralize the system until the system is neutral, and use pH test paper to detect;

[0063] ...

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Abstract

The invention provides a highly-efficient synthetic method for 2, 6-dimethoxy-4-vinylphenol. The method comprises the following steps: with sinapic acid as a raw material and alumina as a solid-phase carrier, carrying out thermal decarboxylation in the presence of an alkaline catalyst under a microwave-assisted condition, adding a polymerization inhibitor to reduce and prevent polymerization of synthetic products, neutralizing the alkaline catalyst in the reaction system when the reaction is completed, extracting the synthetic products with an organic solvent, carrying out washing and drying, then carrying out purifying by using preparative liquid chromatography, and carrying out vacuum drying to obtain high-purity 2, 6-dimethoxy-4-vinylphenol. The highly-efficient synthetic method for 2, 6-dimethoxy-4-vinylphenol provided by the invention has the characteristics of significant improvement of reaction rate, fast temperature rise, convenient operation, high conversion rate, easy purification of the products, etc.; and the synthesized 2, 6-dimethoxy-4-vinylphenol has the properties of high purity, strong oxidation resistance, etc.

Description

technical field [0001] The invention relates to the technical field of food chemical synthesis, in particular to a high-efficiency synthesis method of 2,6-dimethoxy-4-vinylphenol. Background technique [0002] Polyphenolic compounds are a class of secondary metabolites widely present in plants, which play a role in preventing plant ultraviolet radiation damage, resisting pests, viruses and bacteria, and regulating plant hormones during plant growth. Rapeseed is one of the most important oil crops in my country, with an annual planting area of ​​about 120 million mu and a total output of 11-12 million tons, accounting for about 25% of the world. The content of polyphenols in rapeseed is much higher than other oil crops, reaching 2-4%, and the content of defatted rapeseed cake is about 3%, which is about 30 times that of soybean meal. Rapeseed polyphenols are divided into phenolic acids and tannins, of which phenolic acids are further divided into free phenolic acids, soluble...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07C41/18
CPCC07C41/18C07C43/23
Inventor 黄凤洪杨湄郑畅周琦李文林刘昌盛万楚筠
Owner INST OF OIL CROPS RES CHINESE ACAD OF AGRI SCI
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