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Total synthesis method of trans-resveratrol

A technology of total synthesis of resveratrol, which is applied in the field of total synthesis of trans-resveratrol, can solve problems such as easy production of isomers, harsh reaction conditions, and limited source of raw materials, and achieve mild reaction conditions and high product yield. High efficiency and environment-friendly effect

Inactive Publication Date: 2014-02-12
HUNAN KEYUAN BIO PRODS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above methods all have limitations and defects: although the witting reaction conditions are mild, the product yield is low; the heck reaction route is short, but the reaction conditions are harsh, and the source of raw materials is limited; easy to produce isomers

Method used

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Examples

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Embodiment

[0036] This embodiment includes the following steps:

[0037] (1) 3,5-dihydroxybenzoic acid reacts with dimethyl sulfate to generate methyl 3,5-dimethoxybenzoate:

[0038] 10kg anhydrous acetone was first dropped into the dry 50L reactor, then 2.4kg of 3,5-dihydroxybenzoic acid, 10kg of anhydrous potassium carbonate were dropped, after stirring, dimethyl sulfate 5kg was added dropwise, and after 6 hours of stirring reaction , filtered, concentrated and crystallized to obtain 2.8kg of methyl 3,5-dimethoxybenzoate;

[0039] (2) methyl 3,5-dimethoxybenzoate reacts with a reducing agent to prepare 3,5-dimethoxybenzyl alcohol:

[0040] Drop into 15kg of tetrahydrofuran in a dry 50L reactor, add 2kg of anhydrous lithium chloride, 2.2kg of sodium borohydride, stir for 2 hours, then dropwise add the tetrahydrofuran solution of methyl 3,5-dimethoxybenzoate (containing 3,5-dimethoxybenzoic acid methyl ester 2.8kg and tetrahydrofuran 6kg), after reflux reaction for 6 hours, concentrate...

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Abstract

The invention discloses a total synthesis method of trans-resveratrol. The total synthesis method comprises the following steps: (1) enabling 3,5-dihydroxy-benzoic acid to react with dimethyl sulfate, so as to generate 3,5-dimethoxy methyl benzoate; (2) enabling the 3,5-dimethoxy methyl benzoate to react with a reducing agent, so as to prepare 3,5-dimethoxybenzhydrol; (3) carrying out nucleophilic substitution on the 3,5-dimethoxy methyl benzoate and phosphorus tribromide, so as to generate 3,5-dimethoxy benzol benzyl bromide; (4) enabling the 3,5-dimethoxy benzol benzyl bromide to react through witting-horner, so as to prepare 3,5,4-triethoxy toluylene; and (5) preparing the trans-resveratrol from the 3,5,4-triethoxy toluylene. The total synthesis method has the advantages of being wide in material source, mild in reaction condition, friendly to environment, high in product yield, high in purity, applicable to industrialized mass production and the like.

Description

technical field [0001] The invention relates to a total synthesis method of trans-resveratrol. Background technique [0002] Resveratrol, also known as, 3,4',5-trihydroxystilbene, Polygonum aglycone, stilbene; chemical name 3,4',5-trihydroxystilbene or (E)-5-[2 -(4-Hydroxyphenyl)-vinyl]-1,3-benzenediol, molecular formula: C 14 H 12 O 3 , molecular weight: 228.24, CAS number: 501-36-0. Resveratrol was discovered as early as 1940. It is a natural antioxidant existing in plants. It plays an antioxidant role mainly by scavenging or inhibiting the generation of free radicals, inhibiting lipid peroxidation, and regulating the activity of antioxidant-related enzymes. In addition, it also has the functions of anti-arteriosclerosis, anti-thrombosis, protecting cardiovascular and cerebrovascular, anti-inflammatory and antibacterial, preventing liver damage, anti-cancer and anti-mutation. Because of its various biological and pharmacological activities, it is widely used in food,...

Claims

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Application Information

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IPC IPC(8): C07C39/21C07C37/055
CPCC07C37/055C07C41/22C07C41/26C07C41/30C07C67/11C07C39/21C07C43/215C07C43/225C07C43/23C07C69/92
Inventor 李伟刘志强
Owner HUNAN KEYUAN BIO PRODS
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