Preparation of trans-polyhydroxy diphenyl ethylene

The technology of polyhydroxy stilbene and diphenyl acrylic acid is applied in the chemical field, and can solve the problems of hydroxyl group protection and deprotection, low reaction selectivity, high difficulty in industrialization and the like, and achieves low cost, good atom economy, Easy to purify effect

Inactive Publication Date: 2012-11-28
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have some disadvantages, such as strict anhydrous or low-temperature operation, harsh reaction conditions, difficult industrialization, low reaction selectivity, cis-trans isomerization, protection and deprotection of hydroxyl groups, high cost, etc. shortcoming

Method used

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  • Preparation of trans-polyhydroxy diphenyl ethylene
  • Preparation of trans-polyhydroxy diphenyl ethylene
  • Preparation of trans-polyhydroxy diphenyl ethylene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Weigh 3.04g (0.02mol) of 4-hydroxyphenylacetic acid, add 2.76g (0.02mol) of 3,5-dihydroxybenzaldehyde into the reaction flask, dissolve with 12.24g (0.12mol) of acetic anhydride, then add 5.05g (0.05 mol) triethylamine, heated to 110°C, reacted for 6 hours, poured into ice water to precipitate solid, dissolved with 10% sodium hydroxide, washed with ethyl acetate, and crystallized at low temperature after acidifying the water layer to obtain a light yellow solid (E )-2-(4'-hydroxyphenyl)-3-(3',5'-dihydroxyphenyl)-acrylic acid, weighed dry to obtain 4.98g, yield 91.5%, recrystallized with ethanol-water to obtain 4.45 g white crystals, yield 81.8%.

Embodiment 2

[0027] Weigh 4.52g (0.02mol) of 4-hydroxyphenylacetic acid, add 2.21g (0.016mol) of 3,5-dihydroxybenzaldehyde into the reaction flask, dissolve with 8.16g (0.08mol) acetic anhydride, then add 2.02g (0.02 mol) triethylamine, heated to 100°C, reacted for 8 hours, poured into ice water to precipitate solid, dissolved with 10% sodium hydroxide, washed with ethyl acetate, and crystallized at low temperature after acidifying the water layer to obtain a light yellow solid (E )-2-(4'-hydroxyphenyl)-3-(3',5'-dihydroxyphenyl)-acrylic acid, weighed dry to obtain 3.75g, yield 86.2%, recrystallized with methanol-water to obtain 3.11 g pale yellow crystals, yield 71.5%.

Embodiment 3

[0029] Weigh 4.52g (0.02mol) of 4-hydroxyphenylacetic acid, add 3.31g (0.024mol) of 3,5-dihydroxybenzaldehyde into the reaction flask, dissolve with 16.32g (0.16mol) of acetic anhydride, then add 8.08g (0.08 mol) triethylamine, heated to 140°C, reacted for 2 hours, poured into ice water to precipitate solid, dissolved with 10% sodium hydroxide, washed with ethyl acetate, and crystallized at low temperature after acidifying the water layer to obtain a light yellow solid (E )-2-(4'-hydroxyphenyl)-3-(3',5'-dihydroxyphenyl)-acrylic acid, dry and weighed to obtain 4.82g, yield 88.6%, weighted by ethyl acetate-petroleum ether Crystallization gave 4.31 g of light yellow crystals, with a yield of 79.3%.

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Abstract

The invention discloses a preparation method of trans-polyhydroxy diphenyl ethylene. The method comprises the following steps: taking hydroxy-substituted benzaldehyde and hydroxy-substituted phenylacetic acid as raw materials, building up a cis-diphenyl ethylene skeleton by a Perkin reaction, and obtaining the trans-polyhydroxy diphenyl ethylene by decarboxylation and isomerization reaction. The preparation method has the advantages of simple operation, mild reaction condition, good atom economy, high trans-form selectivity, no need of hydroxyl protection and deprotection, easy purification of products, short synthetic route, higher yield, low cost and the like, so the method has good industrialized application prospect.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of trans polyhydroxy stilbene. Background technique [0002] Polyhydroxystilbenes have extensive and beneficial biological activities, and have important scientific research value and broad application prospects as pharmaceutical products. The most representative ones are resveratrol, oxidized resveratrol, piceatannol, etc. The research on these compounds has become a hot spot and frontier in the field of scientific research today. Resveratrol (Resveratrol), the chemical name is (E)-3,4',5-trihydroxystilbene, which has a trans-stilbene skeleton structure, and has attracted much attention in recent years with the ability to activate Sirtuins anti-aging enzymes , anti-cancer, anti-cancer, lowering blood fat, anti-thrombosis, prevention of dementia, anti-oxidation, anti-free radicals, anti-osteoporosis, anti-bacterial and anti-inflammatory, beauty and skin care...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/21C07C37/50
CPCY02P20/55
Inventor 邹永都建立肖春芬
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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