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A kind of preparation method of resveratrol

A technology for resveratrol and compound, which is applied in the field of organic compound synthesis and can solve the problems of serious environmental pollution, expensive raw materials and the like

Active Publication Date: 2021-06-08
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The main methods for synthesizing resveratrol on the market include Wittig method, Heck reaction, and Perking reaction, but they all have disadvantages such as expensive raw materials and serious environmental pollution.

Method used

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  • A kind of preparation method of resveratrol
  • A kind of preparation method of resveratrol
  • A kind of preparation method of resveratrol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The synthetic route of resveratrol (1) is:

[0040]

[0041] Example 1

[0042] The synthetic method of resveratrol (7), the steps are as follows:

[0043] 1) Preparation of 6-[4-hydroxyphenyl]-3,5-hexadien-2-one (compound 2)

[0044] Mix 1 g of p-hydroxycinnamaldehyde, 10 ml of acetone, and 2 ml of 20% sodium hydroxide solution, and stir at room temperature for 3 h. Add water to precipitate a solid, filter and wash with water to obtain the product 6-[4-hydroxyphenyl]-3,5-hexadien-2-one with a yield of over 95%.

[0045] The experimental data are: 1H NMR (400MHz, dmso) δ9.83(s, 1H), 7.42–7.29(m, 2H), 7.00(d, J=15.5Hz, 1H), 6.89(d, J=10.6Hz ,1H),6.77–6.72(m,2H),6.13(d,J=15.5Hz,1H),2.21(s,3H).

[0046] 2) Preparation of 6-[4-phenylbenzyloxy]-3,5-hexadien-2-one (compound 3)

[0047] Mix 1 g of 6-[4-hydroxyphenyl]-3,5-hexadien-2-one, 12 ml of tetrahydrofuran, 0.54 g of potassium carbonate, and 0.72 g of benzyl bromide, stir at reflux at 70°C for 3 h, and quench with...

Embodiment 2

[0062] 1) Preparation of 6-[4-hydroxyphenyl]-3,5-hexadien-2-one (compound 2)

[0063] Mix 5g of p-hydroxycinnamaldehyde, 40ml of acetone, and 9ml of 20% sodium hydroxide solution, and stir at room temperature for 3h. Add water to precipitate a solid, and wash with suction to obtain 6-[4-hydroxyphenyl]-3,5-hexadien-2-one with a yield of over 98%.

[0064] The experimental data are: 1H NMR (400MHz, dmso) δ9.83(s, 1H), 7.42–7.29(m, 2H), 7.00(d, J=15.5Hz, 1H), 6.89(d, J=10.6Hz, 1H), 6.77–6.72(m, 2H), 6.13(d, J=15.5Hz, 1H), 2.21(s, 3H).

[0065] 2) Preparation of 6-[4-phenylbenzyloxy]-3,5-hexadien-2-one (compound 3)

[0066] Mix 5g of 6-[4-hydroxyphenyl]-3,5-hexadien-2-one, 5ml tetrahydrofuran, 3g potassium carbonate and 3.8g benzyl bromide, stir at reflux at 70°C for 3h, add water to quench, and the column layer The p-benzyloxycinnamaldehyde was obtained by analysis, and the yield reached more than 95%.

[0067] The experimental data is: 1 H NMR (400MHz, dmso) δ7.51 (d, J = 8...

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Abstract

The invention relates to a preparation method of resveratrol, which uses p-hydroxycinnamaldehyde as a starting material, not only can obtain higher yield, but also has less pollution and mild reaction conditions. It is a better new method for synthesizing resveratrol.

Description

technical field [0001] The invention relates to the synthesis of organic compounds, in particular to a method for preparing resveratrol. Background technique [0002] Resveratrol is a natural antioxidant that can reduce blood viscosity, inhibit platelet aggregation and vasodilation, keep blood flowing, prevent the occurrence and development of cancer, and have anti-atherosclerosis, coronary heart disease, ischemia Sexual heart disease, prevention and treatment of hyperlipidemia. There are many ways to synthesize resveratrol, and the traditional techniques of resveratrol ((4-hydroxyphenyl)-vinyl]-1,3-benzenediol) are mostly extracted from the rhizomes of natural plants, using cellulose Enzyme for enzymatic hydrolysis. However, the cellulase in the market is very expensive and costly, which is not conducive to industrial production, and this technology faces problems such as limited resources and small production capacity. [0003] There are two main methods for synthesizin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/055C07C39/21C07D309/12C07C45/45C07C49/248
CPCC07C37/055C07C41/26C07C45/45C07C45/64C07C45/65C07C51/09C07C67/343C07D309/12C07C39/21C07C49/248C07C43/23C07C49/753C07C62/38C07C69/757C07C49/255Y02P20/55
Inventor 袁宇蒋程飞黄小根张树伟
Owner YANGZHOU UNIV
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