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Process for synthesizing resveratrol by using de-methylation technology

A technology of resveratrol and demethylation, applied in the fields of organic chemistry and functional food chemistry, can solve the problems of inconvenient industrialized production, use, transportation, storage, harsh reaction conditions, etc., and is conducive to labor protection, The effect of convenient procurement and easy operation

Inactive Publication Date: 2005-09-07
NANJING RALLY BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The only advantage of the boron tribromide demethylation method is the high yield, but the boron tribromide used is a colorless transparent fuming liquid at room temperature, which is easily decomposed by water, alcohol, etc., packaged in a bottle, and stored in a dry and cool place , it is inconvenient to use, transport, and store, and it cannot form industrial scale production, and its price is relatively expensive, lacking the competitive advantage of market value
[0007] The Grignard reagent of methyl iodide is also harsh in reaction conditions, expensive and difficult to produce on an industrial scale; of course there is also a catalyst AlI 3 / CH 3 CN, (Ya Bing Feng, etal, Chinese Chemical Letter, Vol.9 NO.11, 1998, 1003-1004), also useful pyridine / hydrogen bromide / perbromide (A.S.Ijaz etal.Indian.J.Chem.1994 Vol33B228-229), but all have their limitations

Method used

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  • Process for synthesizing resveratrol by using de-methylation technology
  • Process for synthesizing resveratrol by using de-methylation technology
  • Process for synthesizing resveratrol by using de-methylation technology

Examples

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Embodiment 1

[0021] Example 1. Preparation of 3,5,4'-trihydroxyl-1,2-stilbene (resveratrol)

[0022] Add 30Kg 3,5,4'-trimethoxystilbene and 180Kg pure anhydrous pyridine into the reaction kettle, stir and dissolve, heat to raise the temperature slowly, control it at about 100°C, and add trichloride in batches Aluminum, a large amount of heat is released, the temperature is controlled not to exceed 170°C, and the addition of aluminum trichloride is completed in about 1 hour. After the addition, react at 150-165°C for 2-5 hours, complete the reaction time, and use high-performance liquid phase tracking to determine whether the demethylation is complete.

[0023] Pump 1200Kg of water into the hydrolysis kettle, pre-cool to 10°C, stir, put the above reaction solution into the hydrolysis kettle while it is hot under vacuum, and generate a lot of smoke, and remove the gas in time. The hydrolysis reaction solution was cooled to 10°C, centrifuged, and dried. Wash with 50Kg cold water and spin dr...

Embodiment 2

[0024] Example 2. Preparation of 3,5,4'-trimethoxystilbene

[0025] Add 64.3Kg p-methoxybenzyl chloride and 160Kg triethyl phosphite into the enamel reaction kettle respectively, start stirring, set the temperature of the oil bath at 140°C, react for 5-8 hours, and evaporate the triethyl phosphite in a vacuum. Add 400Kg DMF. Then add 48.7Kg of 50% sodium methoxide under cooling, react at 5°C for two hours until dissolved, then add 3,5-dimethoxybenzaldehyde into the reaction kettle, and react at room temperature for 10-12 hours. After the reaction is completed, about 98Kg of the intermediate can be obtained after treatment, with a yield of 90%, HPLC: ≥92%.

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Abstract

The invention relates to a process for synthesizing resveratrol by using de-methylation technology, which comprises using 3,5,4'-trimethoxyl diphenyl ethylene as raw material, using aluminium chloride / pyridine as catalyst for synthesizing Resveratrol through demethyl process, and employing market available methoxyl benzyl chloride for Wittig reaction with 3,5- dimethoxybenzaldehyde, thus preparing intermediate 3,5,4'-trimethoxyl diphenyl ethylene.

Description

field of invention [0001] The invention relates to the fields of organic chemistry and functional food chemistry, in particular, the invention relates to a new demethylation process synthesis method of resveratrol, a trihydroxystilbene functional food. Background technique [0002] Chemical name of resveratrol: 3,5,4'-trihydroxy-1,2-stilbene, also known as 3,5,4'-trihydroxystilbene, English name: Resveratrol, CAS: [501-36 -0], molecular formula: C 14 h 12 o 3 , molecular weight: 228.25. It is a multifunctional health food that exists in various plants such as grapes, knotweed, cassia, and peanuts. Resveratrol has extremely strong antioxidant properties, can effectively eliminate free radicals, and inhibit various oxidation reactions that cause atherosclerosis and thrombosis, thereby significantly improving the function of human endothelial cells, thus playing an important role in the prevention and treatment of cardiovascular diseases. important role in disease. In 200...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/00C07C39/21
Inventor 陈新梅以成张荣根俞爱民
Owner NANJING RALLY BIOCHEM
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