Method for modifying synthetic veratric alcohol

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

Inactive Publication Date: 2007-09-12
NANJING RALLY BIOCHEM
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  • Description
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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 Vol33B 228-229), but all have their limitations

Method used

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  • Method for modifying synthetic veratric alcohol
  • Method for modifying synthetic veratric alcohol
  • Method for modifying synthetic veratric alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0021] Embodiment 1.3,5,4'-trihydroxyl-1,2-stilbene (resveratrol) preparation

[0022] Add 30g (0.11mol) of 3,5,4'-trimethoxystilbene and 75g of pure anhydrous pyridine into the reaction kettle, stir and dissolve, heat to raise the temperature slowly, control it at about 100°C, and batch After adding aluminum trichloride, a large amount of heat is released, the temperature is controlled not to exceed 170°C, and the addition of aluminum trichloride (total amount 95g.0.66mol) is completed in about 1 hour. After the addition, react at 150-165°C for 3 hours.

[0023] Pump 1200g 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 50g of cold water and spin dry. The crude product was obtained, which was recrystallized with acetone to obtain 1...

Embodiment 2

[0024] Embodiment 2. Preparation of resveratrol

[0025] Add 30g (0.11mol) of 3,4',5-trimethoxystilbene, 75g of pure anhydrous pyridine, 15g of trimethylbenzene, and 3g of hydroquinone into the reactor, stir and dissolve, and heat to raise the temperature slowly. Control at about 100°C, add anhydrous aluminum trichloride in batches, a large amount of heat is released, control the temperature not to exceed 170°C, and add anhydrous aluminum trichloride (total amount: 95g.0.66mol) in about 1 hour. After the addition, react at 150-165°C for about 3 hours, and distill off trimethylbenzene under reduced pressure.

[0026] Pump 1200g 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 50g of cold water and spin dry. The crude product was obtai...

Embodiment 33

[0027] Embodiment 3.3,5, the preparation of 4'-trimethoxystilbene

[0028] Add 64.3Kg of p-methoxybenzyl chloride and 160g of 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 400g DMF. Then add 48.7g 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 98g of the intermediate can be obtained after treatment, with a yield of 90% and a content (HPLC) ≥ 92%.

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Abstract

This invention relates to an improved method for synthesizing resveratrol, which takes 3, 5, 4'-methylate toluylene as the raw material, 1, 3, 5-trimethylbenzene as the solvent and hydroquinone as the antioxidant to synthesize resveratrol with alchlor/pyridine as the catalyst and applies commercial cheap anisyl chlorben and 3, 5-dimethoxy benzene formaldehyde for wittig reaction to prepare an intermediate 3, 5, 4'-methylate toluylene.

Description

field of invention [0001] The invention relates to the fields of organic chemistry and functional food chemistry, in particular, the invention relates to an improved 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 2000, Ameri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/055C07C39/21
Inventor 陈新梅以成俞爱民王凯文
Owner NANJING RALLY BIOCHEM
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