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Synthesis method of resveratrol

A technology of resveratrol and dihydroxybenzyl alcohol, which is applied in the chemical industry, can solve the problems of high cost, complex process, and difficult separation, and achieve the effects of low cost, simple operation, and good reaction yield

Inactive Publication Date: 2016-06-01
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a method for preparing resveratrol, and the method for preparing resveratrol in the prior art should solve the method for preparing resveratrol in the prior art Technical problems such as complex process, difficult separation and high cost

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] This reaction should be carried out under the protection of nitrogen, and try to keep the reaction system anhydrous. Add 5 g of sodium borohydride (132 mmol) and 54.5 g of ethylene glycol dimethyl ether into the reactor, and stir to make the sodium borohydride evenly disperse in the ethylene glycol dimethyl ether solution. Take by weighing 6.8g (44mmol) 3,5-dihydroxybenzoic acid is dissolved in the 34g ethylene glycol dimethyl ether solution, it is slowly added dropwise in the ethylene glycol dimethyl ether solution of sodium borohydride (within one hour After dripping), keep the temperature between 25-30°C. After the dropwise addition was complete, stirring was continued at room temperature for 1.5 hours. Next, 25 g (172 mmol) of boron trifluoride in ether was slowly added dropwise to the reaction system, and the addition was completed in about an hour, and the temperature was maintained at 25-30°C. After the dropwise addition was completed, the reaction was carried ...

Embodiment 2

[0036] Add 5g (35.7mmol) of 3,5-dihydroxybenzyl alcohol and 300mL of anhydrous acetonitrile successively into a 1L three-necked flask equipped with a thermometer and a condenser, start stirring, and add 12.2g (35.7mmol) of triphenyl Phosphine hydrobromide. The oil bath was heated to reflux, and the heating was stopped after 12 hours, and the reaction system was cooled to room temperature. Then the temperature in the reaction system was lowered to 0° C. under an ice-water bath, and continued to stir at this temperature for 30 minutes. At this time, it was found that a large amount of white solids were precipitated, filtered, and the filter cake was once cooled with low-temperature acetonitrile, and then Washed with anhydrous ether, and then dried, the dried solid product was 18.6g, and the yield was 72.3%.

[0037] 1 HNMR (300MHz, d 6-DMSO): d: 9.35ppm (2H, s), 7.94-7.63ppm (15H, m), 6.17-6.16ppm (1H, d, J = 2.09Hz), 5.82-5.80ppm (2H, t, J = 2.24Hz),4.92-4.87(2H,d,J=15.64Hz...

Embodiment 3

[0039] The solid 9.31g (20mmol) obtained in Example 2, 2.44g (20mmol) of p-hydroxybenzaldehyde, 7.41g (66mmol) of potassium tert-butoxide and 100 ml of dried anhydrous tetrahydrofuran were added to the reactor, while Heat up to 80°C while stirring, continue the reaction at this temperature until the reaction is substantially complete (about 20-24 hours), cool to room temperature, add 6g (5.2ml, 60mmol) of 36.5% concentrated hydrochloric acid, and continue stirring at room temperature React for 30 minutes. Filtrate, wash the filter residue with methyl tert-butyl ether, wash the filtrate with water, concentrate under reduced pressure to remove the solvent, and recrystallize the obtained crude product with ethanol-water to obtain a white solid of resveratrol, weight 3.42g, yield 75% .

[0040] 1 HNMR (300MHz, d 6 -DMSO)d9.59(bs,1H),9.23(bs,2H),7.42(d,J=8.70Hz,2H),6.97(d,J=16.5Hz,1H),6.85(d,J=16.5 Hz, 1H), 6.78(d, J=8.40Hz, 2H), 6.43(d, J=2.10Hz, 2H), 6.16(t, J=2.10Hz, 1H); 1...

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Abstract

The invention provides a synthesis method of resveratrol.The method includes the steps of dissolving 3,5-dihydroxybenzoic acid in solvent, conducting reaction on sodium borohydride and Lewis acid to obtain 3,5-dihydroxy-benzyl alcohol, conducting reaction on 3,5-dihydroxy-benzyl alcohol and triphenylphosphine hydrobromic acid in certain solvent to obtain corresponding phosphonium, and making the obtained phosphonium react with p-hydroxy benzaldehyde under the effect of strong alkali to directly obtain the product resveratrol.The preparation method includes few steps, precious metal catalysts are prevented from being used in protection and deprotection processes of phenolic hydroxyl groups in the technology, cost is low, operation is easy, reaction conditions are easy to achieve, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of chemical industry and relates to a kind of resveratrol, in particular to a preparation method of resveratrol. Background technique [0002] Resveratrol (I) is a non-flavonoid polyphenolic compound containing a stilbene structure. It is not only a phytoalexin, but also a beneficial drug in many aspects such as anti-cancer, anti-oxidation, regulating blood lipids, and affecting lifespan. A substance with an important function in human health. [0003] [0004] Because resveratrol has a wide range of uses, its market demand and potential are particularly large. Although it can be extracted from some plants, this method of extracting from nature and the method of preparing resveratrol with biotechnology methods studied by people later cannot meet the needs of the market far away. Therefore must just can satisfy people's needs to this product by means of the method for chemical synthesis. At present, there are man...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/20C07C39/21C07C37/00C07C39/11C07F9/54
CPCC07C37/002C07C37/20C07F9/5456C07C39/21C07C39/11
Inventor 欧文华张婉萍
Owner SHANGHAI INST OF TECH
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