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Preparation of trans-polyhydroxy diphenyl ethylene

A technology of polyhydroxy stilbene and hydroxyphenylacetic acid, which is applied in the field of preparation of trans polyhydroxy stilbene, can solve the problems of protection and deprotection of hydroxyl groups, low reaction selectivity, harsh reaction conditions, etc. low cost, good atom economy, and short synthetic route

Inactive Publication Date: 2011-07-20
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

[0032] Weigh 5.88g (0.02mol) of 3,5-dibromophenylacetic acid, add 2.44g (0.02mol) of p-hydroxybenzaldehyde into the reaction flask, dissolve with 8.16g (0.08mol) of acetic anhydride, then add 5.05g (0.05mol) ) 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 light yellow solid (E) -2-(3',5'-dibromophenyl)-3-(4'-hydroxyphenyl)-acrylic acid, weighed dry to obtain 7.28g, yield 91.5%, recrystallized with ethanol-water to obtain 6.51g White crystals, yield 81.8%.

Embodiment 2

[0034] Weigh 5.88g (0.02mol) of 3,5-dibromophenylacetic acid, add 1.95g (0.016mol) of p-hydroxybenzaldehyde into the reaction flask, dissolve with 4.08g (0.04mol) of acetic anhydride, and then add 2.02g (0.02mol) ) 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 light yellow solid (E) -2-(3',5'-dibromophenyl)-3-(4'-hydroxyphenyl)-acrylic acid, weighed dry to obtain 5.49g, yield 86.2%, recrystallized from methanol-water to obtain 4.55g White crystals, yield 71.5%.

Embodiment 3

[0036] Weigh 5.88g (0.02mol) of 3,5-dibromophenylacetic acid, add 2.93g (0.024mol) of p-hydroxybenzaldehyde into the reaction flask, dissolve with 12.24g (0.12mol) of acetic anhydride, then add 8.08g (0.08mol) ) 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 light yellow solid (E) -2-(3',5'-dibromophenyl)-3-(4'-hydroxyphenyl)-acrylic acid, weighed dry to obtain 7.02g, yield 88.2%, recrystallized from ethyl acetate-petroleum ether 4.31 g of white crystals were obtained, with a yield of 79.3%.

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PUM

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Abstract

The invention discloses a method for preparing trans-form polyhydroxy phenethylene. The method uses (bromo) hydroxy benzaldehyde and (bromo) hydroxyphenylacetic acid as raw materials, utilizes Perkin reaction to construct a syn-form diphenyl ethylene skeleton, and then obtains the trans-form polyhydroxy phenethylene through functional group conversion and decarboxylation-isomerization reaction. The method has the advantages of simple operation, mild reaction conditions, good atom economy, high trans-form selectivity, no need of hydroxyl protection, easy purification for the products, short synthetic route, high yield, low cost, and the like, and has favorable 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): C07C39/215C07C37/50
Inventor 邹永都建立孙洪宜
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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