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Oxyresveratrol synthesis method

A technique for oxidizing resveratrol and a synthetic method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of harsh reaction conditions, low yield, expensive raw materials, etc., and achieve low cost and high yield. The effect of high efficiency and easy access to raw materials

Inactive Publication Date: 2016-03-23
SHAANXI JIAHE PHYTOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic method also has many disadvantages such as complicated steps, expensive raw materials, harsh reaction conditions and low yield.

Method used

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  • Oxyresveratrol synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0019] 1, 3, the preparation of 5-dimethoxybenzyl chloride

[0020] Put 42g of 3,5 dimethoxybenzyl alcohol and 126ml of phosphorus oxychloride into a dry 500ml four-necked reaction flask, heat up and reflux for about 2 hours, TLC detection, the raw materials are basically reacted, pressurize and recover the solvent to 1 / 3 and cool down To 0-5°C, slowly add 150ml of water dropwise, after the addition is complete, stir at room temperature for 2h, filter, wash with water to neutralize, and dry under reduced pressure to obtain 45g of white solid with a yield of 96.7%.

[0021] 2. Preparation of tetramethoxystilbene

[0022] In a dry 500ml four-necked reaction flask, put 37.2g of 3,5-dimethoxybenzyl chloride, 27g of trimethyl phosphite, and 80ml of DMF, heat up and reflux for 4.5h, TLC detection, raw material 3,5-dimethoxy Benzyl chloride disappeared. Cool down to 5-10°C, add 29.8g of 28% sodium methoxide solution dropwise, keep stirring at this temperature for 2h after dropping,...

Embodiment 2

[0026] 1, 3, the preparation of 5-dimethoxybenzyl chloride

[0027] Put 42g of 3,5 dimethoxybenzyl alcohol and 150ml of phosphorus oxychloride into a dry 500ml four-necked reaction flask, heat up and reflux for about 2 hours, TLC detection, the raw materials are basically reacted, pressurize and recover the solvent to 1 / 3 and cool down To 0-5°C, slowly add 180ml of water dropwise, after the addition is complete, stir at room temperature for 2h, filter, wash with water to neutralize, and dry under reduced pressure to obtain 42.5g of white solid with a yield of 91.3%.

[0028] 2. Preparation of tetramethoxystilbene

[0029] In a dry 500ml four-necked reaction flask, put 37.2g of 3,5-dimethoxybenzyl chloride, 26g of trimethyl phosphite, and 120ml of DMF, heat up and reflux for 4 hours, TLC detection, raw material 3,5-dimethoxychloride Benzyl disappears. Cool down to 5-10°C, add 30g of 28% sodium methoxide solution dropwise, keep stirring at this temperature for 2h after droppin...

Embodiment 3

[0033] 1, 3, the preparation of 5-dimethoxybenzyl chloride

[0034] Put 42g of 3,5 dimethoxybenzyl alcohol and 175ml of phosphorus oxychloride into a dry 500ml four-necked reaction flask, heat up and reflux for about 4 hours, TLC detection, the raw materials are basically reacted, pressurize and recover the solvent to 1 / 3 and cool down To 0-5°C, slowly add 200ml of water dropwise, after the addition is complete, stir at room temperature for 2h, filter, wash with water to neutralize, and dry under reduced pressure to obtain 43.0g of white solid with a yield of 93.6%.

[0035] 2. Preparation of tetramethoxystilbene

[0036]Into a dry 500ml four-necked reaction flask, put 37.2g of 3,5-dimethoxybenzyl chloride, 35g of trimethyl phosphite, 90ml of DMF, heat up and reflux for 2.5h, TLC detection, raw material 3,5-dimethoxy Benzyl chloride disappeared. Cool down to 5-10°C, add 44g of 28% sodium methoxide solution dropwise, keep stirring at this temperature for 2h after dropping, ad...

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Abstract

The invention provides an oxyresveratrol synthesis method which comprises the following steps: firstly performing a reflux reaction between raw materials 3,5-dimethoxybenzyl alcohol and phosphorus oxychloride; after the reaction is complete, pressurizing and recycling the solvent; filtering, washing to neutrality and drying to obtain 3,5-dimethoxybenzyl chloride; performing a reflux reaction between the obtained 3,5-dimethoxybenzyl chloride and trimethyl phosphite in a solvent DMF (dimethyl formamide); after the reaction is complete, adding a catalyst sodium methylate solution, and adding a mixed solution of 2,4-dimethoxy benzaldehyde and DMF to obtain tetramethoxy diphenyl ethylene; and finally, performing a reflux reaction between the obtained tetramethoxy diphenyl ethylene and aluminum trichloride and xylene, wherein oxyresveratrol is obtained after the reaction is complete. According to the method provided by the invention, a Witting-Homer reaction is adopted, the raw materials are easily available, the yield is high, the cost is low, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for synthesizing oxidized resveratrol. Background technique [0002] Oxidized resveratrol, English name: Oxyresveratrol, chemical name 4-[(E)-2-(3,5-dihydroxyphenyl)vinyl]benzene-1,3-diol. Oxidized resveratrol is a derivative of resveratrol, a natural product of polyhydroxy trans-stilbenes. The natural compound trans-stilbenes have various biological activities such as anti-cancer effects, and are useful for the treatment of cardiovascular diseases. It has excellent curative effect on diseases, viral infections, diabetes, central nervous system disorders, weight loss, anti-inflammation and other diseases. Oxidized resveratrol is an effective tyrosine inhibitor. In addition, it also has a strong skin pigmentation effect, as well as anti-herpes, anti-virus, anti-oxidation, protection of nerves, and inhibition of cells when cerebral ischemia occurs. In addition, oxidize...

Claims

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Application Information

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IPC IPC(8): C07C37/055C07C39/21
CPCC07C41/22C07C37/055C07C41/30C07C43/225C07C43/215C07C39/21
Inventor 肖金霞郭文华靳莎杨雪峰
Owner SHAANXI JIAHE PHYTOCHEM
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