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Preparation method for 3,5-dimethoxy-2,6-biacyl phenol

A technology of diacylphenol and -diacylphenol, which is applied in the field of preparation of 3,5-dimethoxy-2,6-diacylphenol, can solve the problems of long reaction route, low product purity and complex process, etc. Achieve the effects of less waste, high commercial value, low price and easy availability

Active Publication Date: 2014-04-16
INSIGHT HIGH TECH (BEIJING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The purpose of this invention is to provide a kind of preparation method of 3,5-dimethoxyl-2,6-diacylphenol, to overcome the long reaction route existing in the prior art, complex process, low yield and low product purity And other issues

Method used

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  • Preparation method for 3,5-dimethoxy-2,6-biacyl phenol
  • Preparation method for 3,5-dimethoxy-2,6-biacyl phenol
  • Preparation method for 3,5-dimethoxy-2,6-biacyl phenol

Examples

Experimental program
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Effect test

Embodiment 1

[0024] In a 250ml three-necked flask, add 50g of dichloroethane, 16.8g of 1,3,5-trimethoxybenzene, 28g of anhydrous aluminum trichloride, stir and cool down to -10°C; add 15g of acetyl chloride dropwise, and control the reaction temperature- 10~-5°C; heat preservation reaction for 2 hours, then rise to room temperature and stir for 15 hours, slowly pour into 60g of glacial hydrochloric acid with a concentration of 10%, stir, separate liquids, wash the organic phase twice with water and desolvate under reduced pressure to obtain The product is light yellow solid 23g, content 99.1%, melting point 123-124°C, elemental analysis C 12 h 14 o 5 , calculated value (%): C, 60.5; H, 5.92; measured value (%): C, 60.3; H, 6.50; 1 H-NMR (CDCl 3 ,300MHz) δ5.98(s,1H),3.92(s,6H),2.56(s,6H). The yield is 97%.

Embodiment 2

[0026] In a 250ml three-necked flask, add 50g of dichloromethane, 16.8g of 1,3,5-trimethoxybenzene, 53g of anhydrous boron tribromide, stir and cool down to 0°C; add 15g of acetyl chloride dropwise, and control the reaction temperature from 0 to 10°C. ℃; heat preservation reaction for 8 hours, slowly poured into 60g of glacial hydrochloric acid with a concentration of 10%, stirred and separated, and the organic phase was washed twice with water and desolvated under reduced pressure to obtain 22.7g of the product with a content of 98.5% and a yield of 95.5%.

Embodiment 3

[0028] In a 250ml three-necked flask, add 80g of nitrobenzene, 16.8g of 1,3,5-trimethoxybenzene, 28g of anhydrous aluminum trichloride, stir and add 15g of acetyl chloride, the reaction temperature is 60-70°C; keep the temperature for 2 hours, Slowly poured into 60 g of glacial hydrochloric acid with a concentration of 10%, stirred and separated, and the organic phase was washed twice with water and precipitated under reduced pressure to obtain 23.4 g of the product with a content of 98.0% and a yield of 98.6%.

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Abstract

The invention relates to a preparation method for 3,5-dimethoxy-2,6-biacyl phenol. According to the preparation method, 1,3,5-trimethoxy benzol reacts with acyl chloride in an organic solvent under the existence of Lewis acid catalyst. The 3,5-dimethoxy-2,6-biacyl phenol is obtained in one step; the yield is more than 95%; the purity of the product is more than 98%; and the preparation method has the characteristics of easily obtained raw material, low production cost, simple process, environmental protection, and the like.

Description

technical field [0001] The invention relates to a synthesis method of a flavonoid compound intermediate, namely 3,5-dimethoxy-2,6-diacylphenol. Background technique [0002] There are many compounds with medicinal value in flavonoids, such as rutin in Sophora japonica and Nobiletin in tangerine peel, which can reduce the fragility of blood vessels, improve the permeability of blood vessels, reduce blood lipids and cholesterol, and are used to prevent and treat senile hyperlipidemia. Blood pressure and cerebral hemorrhage. Using 3,5-dimethoxy-2,6-diacylphenol (structural formula 1) as a raw material, a series of flavonoids can be synthesized, which have potential or proven medicinal value, such as compounds of structural formula 2 and structural formula 3. [0003] [0004] Structural formula 1 Structural formula 2 [0005] [0006] Structural formula 3 [0007] The preparation method of 3,5-dimethoxy-2,6-diacylphenol has few references, and in the d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/84C07C45/46
Inventor 麻忠利赵文超胡伟静
Owner INSIGHT HIGH TECH (BEIJING) CO LTD
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