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Method for synthesizing trans-resveratrol

A technology of resveratrol and reaction time, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of high price, poor stability, and large dosage of boron tribromide

Inactive Publication Date: 2009-07-08
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In reaction step 4, low temperature is required, the price of raw material boron tribromide is high, the stability is poor, and the consumption is large, so it is not suitable for industrial production

Method used

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  • Method for synthesizing trans-resveratrol
  • Method for synthesizing trans-resveratrol
  • Method for synthesizing trans-resveratrol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Step 1): In a 250ml three-necked flask, 30g of 3,5-methoxybenzyl alcohol was dissolved in a mixed solution of 100ml of DMF and 10ml of triethylamine, and 27ml of thionyl chloride was added dropwise in a water bath at 20°C using a constant pressure dropping funnel (The molar ratio of 3,5-methoxybenzyl alcohol to thionyl chloride is 1:2), after 1 hour of dropwise addition, keep stirring for 4 hours, pour the solution into water at 0°C, precipitate solid, and filter out the solid , washed the solid with water until neutral, and dried it under vacuum at 50° C. for 2 hours to obtain 32.2 g of white crystals, with a yield of 96.7%.

[0027] Step 2): A 250ml three-necked flask was connected to a reflux condenser, and 32.2g of the unpurified product of step 1) and 120ml of triethyl phosphite were added, stirred and reacted in an oil bath at 120°C for 5 hours, then vacuum distilled at 80°C with a vacuum of 5torr , until no liquid was distilled off to obtain 48.3 g of red oily li...

Embodiment 2

[0033] Step 1): In a 250ml three-necked flask, 35g of 3,5-methoxybenzyl alcohol was dissolved in a mixed solution of 100ml of DMF and 5ml of triethylamine, and 23.5ml of thionyl chloride was added dropwise using a constant pressure dropping funnel in a 20°C water bath (The molar ratio of 3,5-methoxybenzyl alcohol to thionyl chloride is 1:1.5), after 1 hour of dropwise addition, keep stirring for 3 hours, pour the solution into 0°C water, precipitate solid, and filter out the solid , washed the solid with water until neutral, and dried it under vacuum at 50° C. for 2 hours to obtain 36.6 g of white crystals, with a yield of 94.2%.

[0034] Step 2) 3) 4) is basically the same as embodiment 1, the difference is

[0035] In step 4), N-methylformylaniline and aluminum trichloride were used as catalysts and reacted at 120° C. for 4 hours; 50 ml of ethanol: water = 1: 1.5 mixed solvent was used for recrystallization.

Embodiment 3

[0037] Step 1): In a 250ml three-necked flask, dissolve 26g of 3,5-methoxybenzyl alcohol in a mixed solution of 100ml of DMF and 30ml of triethylamine, add 35ml of thionyl chloride dropwise in a water bath at 20°C using a constant pressure dropping funnel (The molar ratio of 3,5-methoxybenzyl alcohol to thionyl chloride is 1:3), after 1 hour of dropwise addition, keep stirring for 5 hours, pour the solution into water at 0°C, precipitate solid, and filter out the solid , washed the solid with water until neutral, and dried it under vacuum at 50° C. for 2 hours to obtain 27.5 g of white crystals, with a yield of 95.4%.

[0038] Step 2) 3) 4) is basically the same as embodiment 1, the difference is

[0039] In step 4), react at 140° C. for 6 hours; use 50 ml of ethanol: water = 1:2 mixed solvent for recrystallization.

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Abstract

The invention relates to a method for synthesizing trans-resveratrol as a functional food additive, which is characterized in that 3,5-methoxybenzylchloride is obtained after 3,5-methoxybenzylalcohol is chloro-substituted in DMF-triethylamine mixed solvent; 3,5-methoxy benzyl diethyl phosphate is obtained after the 3,5-methoxybenzylchloride reacts with triethyl phosphite; 3,4',5-trimethoxy toluylene is obtained after reaction products and anisic aldehyde are subjected to Witting reaction; and the trans-resveratrol is generated by removing methoxyl under the catalysis of N-methylaniline and aluminium trichloride. The method has the advantages of economical and readily available raw materials, mild reaction conditions, easy product purification, high reaction yield, friendliness to environment, simple operation and the like, thereby adapting to industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for synthesizing functional food additive trans-resveratrol. Background technique [0002] Trans-resveratrol is a stilbene compound, a phytoalexin produced by plants of the genus Vitis, and its structure is similar to the estrogen acetool. Trans-resveratrol is widely distributed in plants and its content is relatively high. At present, trans-resveratrol has been found in at least 70 kinds of plants. With the in-depth research on trans-resveratrol, it has been found that it has a variety of pharmacological activities, including antioxidant activity, anti-platelet aggregation, anti-atherosclerosis, anti-inflammatory, estrogen-like activity, growth inhibitory activity, immune regulation and antitumor activity. The structure of this compound is as follows: [0003] [0004] Trans-resveratrol is generally extracted from plants, and some progress has been made in chemic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07C37/055
Inventor 龚祝南陈重王可人刘钦龙吴子刚
Owner NANJING NORMAL UNIVERSITY
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