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Synthesis method of resveratrol

A synthetic method, the technology of resveratrol, which is applied in the field of natural product synthesis, can solve the problems of high price and achieve the effect of simple post-treatment, simple operation and post-treatment, and high trans-stereoselectivity

Inactive Publication Date: 2018-03-27
CHANGZHOU UNIV
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Problems solved by technology

However, because the two intermediates required for the Heck reaction are very expensive, it has also become an important reason why the Heck reaction is limited in use! Therefore, in the synthesis from resveratrol, we designed a method using cheap raw materials to synthesize the two expensive intermediates required for the Heck reaction, and then synthesized resveratrol

Method used

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  • Synthesis method of resveratrol
  • Synthesis method of resveratrol
  • Synthesis method of resveratrol

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Experimental program
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Embodiment Construction

[0032] Experimental part

[0033] (1) Synthesis of 12

[0034] Add 3,5-dimethoxybenzoic acid (10.0 g (gram), 55 mmol (mmol)) into a 500 mL (milliliter) round bottom flask, then add 50 mL of thionyl chloride to dissolve it, and heat at 90° C. ) Reflux for 2h (hours) (TLC (thin layer chromatography) tracking). After the reaction, the thionyl chloride was evaporated to dryness under reduced pressure at 60°C to obtain 11 g of brown oily substance 12, which was directly used in the next step without purification.

[0035] (2) Synthesis of 13

[0036] Add 50mL of ammonia water to a 500mL round-bottomed flask, ice-bath for 20 minutes, dissolve 12 (11.0g, 55mmol) in 50mL of acetonitrile and slowly add it dropwise to the three-necked flask, during which a large amount of white solids are produced. After the addition is complete, react at room temperature for 1.5h ( TLC trace). After the reaction was completed, it was transferred to a round-bottomed flask, and the acetonitrile was e...

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Abstract

The invention provides a synthesis method of resveratrol, and belongs to the technical field of natural product synthesis. The synthesis method comprises the following steps: with 3,5-dimethoxy benzoic acid as a raw material, generating 3,5-dimethoxy benzoyl chloride (12) through an acylating chlorination reaction; generating 3,5-dimethoxy benzamide (13) through an amidation reaction of the (12);generating 3,5-dimethoxyaniline (14) through a Hofmann degradation reaction of the (13); generating 3,5-dimethoxy iodobenzene (15) through a Sandmeyer reaction on the (14); generating 3,5,4'-trimethoxy diphenylethene (31) through a reaction between the (15) and p-methoxystyrene (23), and performing demethylation of the (31) to finally obtain resveratrol (1), wherein total yield is 23.3%. Accordingto the method, the adopted reagent is cheap and easily available, aftertreatment is simple, and two expensive intermediates for Heck reaction are synthesized by adopting cheap raw materials. A new synthesis method is provided for synthesizing resveratrol.

Description

technical field [0001] The invention provides a method for synthesizing resveratrol, belonging to the technical field of natural product synthesis. Background technique [0002] Resveratrol is a non-flavonoid polyphenolic compound that has anti-disease and various health functions, and is beneficial to human health. Currently commercially available resveratrol is mostly extracted and isolated from natural plants, but considering the shortcomings of high cost and limited plant resources, the development of chemical synthesis methods for poly-resveratrol has made great progress in recent years. progress. The key to the synthesis of resveratrol is the coupling reaction of two benzene rings, that is, the synthesis of the stilbene skeleton. In addition, the problem of cis-trans isomerism should also be considered. There are mainly Wittig (Wittig) reaction, Wittig-Horner (Witi Horner) reaction, Perkin (Pulkin) reaction and Heck (Heck) reaction. The following is the specific sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/60C07C65/21C07C231/02C07C235/60C07C213/00C07C217/84C07C41/22C07C43/225C07C41/30C07C43/215C07C41/26C07C43/23C07F9/54
CPCC07C41/22C07C41/26C07C41/30C07C51/60C07C213/00C07C231/02C07F9/5442C07C65/21C07C235/60C07C217/84C07C43/225C07C43/215C07C43/23
Inventor 胡昆闫雪龙任杰
Owner CHANGZHOU UNIV
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