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Preparation method for resveratrol

A technology of resveratrol and methoxybenzaldehyde dimethyl acetal is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry and other directions, and can solve the problems of long synthesis lines, high production costs, environmental pollution and the like, Achieve the effect of good quality, low preparation cost and short process flow

Active Publication Date: 2014-03-26
HUNAN KEYUAN BIO PRODS
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Problems solved by technology

[0015] In recent years, although domestic scholars have conducted in-depth research on the chemical synthesis of resveratrol, the yield of resveratrol has been continuously improved through synthetic methods and improved routes, but the existing methods of chemical synthesis of resveratrol are different. However, there are problems such as long synthesis lines, high production costs, and serious environmental pollution.

Method used

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  • Preparation method for resveratrol

Examples

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reference example 1

[0034] Reference example 1: the preparation of raw material p-methoxybenzaldehyde dimethyl acetal:

[0035] In a 500ml three-neck flask equipped with a thermometer and stirring, carefully add 30 grams of p-methoxybenzaldehyde and 210ml of anhydrous methanol, cool to 0°C, replace with nitrogen three times, start stirring, and carefully pass in dry bromine About 20g of hydrogen hydride gas was allowed to stabilize for 1 hour. After the reaction of the raw material was detected by TLC, it was concentrated under reduced pressure to constant weight to obtain 33g of yellow oil, yield: 99%, and stored at low temperature for future use.

[0036] EI-MS(m / z):182[M+H];1HNMR(CH3Cl-D):δ(ppm)7.1(d,2H),5.5(d,1H,),6.7(m,2H,), 3.4(d, 6H,), 3.7(s, 3H).

Embodiment 1

[0038]In a 500ml three-necked flask equipped with a thermometer and a stirrer, 40g of 3,5-dimethoxyphenylacetic acid and 200ml of toluene were added to 43g of p-methoxybenzaldehyde dimethyl acetal in the reaction flask, and 10mL was added dropwise. Acetic anhydride, after the dropwise addition, add 3g triethylamine, reflux for 2 hours; after the reaction of the raw materials is detected by TLC, add 20ml quinoline and 5g copper powder, heat and reflux for 12 hours, after the plate decarboxylation is completed, add 40g of triethylamine in 5 batches Anhydrous aluminum chloride, when adding, control the temperature below 60°C. After the addition, raise the temperature to 70°C, and react for 10 hours. After the reaction of the raw materials is detected by TLC, the developing agent: EA / PE=2:1, carefully added to 2L ice water, the temperature does not exceed 40°C when adding, filter, separate toluene layer, adjust the pH of the water layer to 1-2 with concentrated hydrochloric acid, e...

reference example 2

[0042] Reference example 2 The preparation of raw material p-methoxybenzaldehyde ethylene acetal:

[0043] In a 500ml three-necked flask equipped with a thermometer and stirring, carefully add 30 grams of raw material p-methoxybenzaldehyde and 210ml of anhydrous ethylene glycol, after cooling to 0°C, replace with nitrogen three times, start stirring, and carefully pass through to dry About 20g of hydrogen bromide gas was allowed to stabilize for 1 hour. After the reaction of the raw material was detected by TLC, it was directly passed through the column. The eluent was PE / EA=3:1. After concentration, 28g of yellow oil was obtained. Yield: 92% , stored at low temperature for later use.

[0044] EI-MS(m / z):180[M+H];1HNMR(CH3Cl-D):δ(ppm)7.1(d,2H),5.5(d,1H,),6.7(m,2H,), 3.9(d, 4H,), 3.7(s, 3H).

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Abstract

The invention provides a preparation method for resveratrol. The method comprises the following steps: with (3,5-dimethoxyphenyl)acetic acid as a raw material, subjecting (3,5-dimethoxyphenyl)acetic acid and methoxybenzaldehyde dimethyl acetal to a one-pot reaction so as to obtain a crude resveratrol product; and then carrying out neutralizing with alkali lye, decoloring in alcohol and recrystallization so as to prepare a refined resveratrol product. Compared with the prior art, the preparation method provided by the invention has the advantages of short process flow, simple operation and suitability for industrial production, and the prepared refined resveratrol product has yield of more than 93%, a melting point of 261 to 263 DEG C, HPLC of greater than 99%, a whitish color, good quality and low preparation cost.

Description

technical field [0001] The invention relates to a method for preparing resveratrol, in particular to a method for preparing resveratrol by adopting a one-pot method. Background technique [0002] Resveratrol is stilbene, its English name: (E)-3,4',5-Trihydroxystilbene, chemical name: (E)-5-[2-(4-hydroxyphenyl)-vinyl]- 1,3-benzenediol, the structural formula is as follows: [0003] [0004] Resveratrol is a non-flavonoid polyphenolic compound containing a stilbene structure. Biological and medical research shows that resveratrol has various pharmacological activities and health functions beneficial to human health, such as anti-tumor, anti-oxidation, anti-virus, anti-inflammatory and anti-bacterial, immune liver protection, treatment of cardiovascular diseases, plant Estrogen, etc., can be widely used in medicine, health food and cosmetics and other fields, and its market demand is very large, and it is increasing day by day. Although resveratrol has been found in mor...

Claims

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Application Information

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IPC IPC(8): C07C39/21C07C37/055
CPCC07C37/055C07C41/30C07C39/21C07C43/215
Inventor 杨昌勇刘志强
Owner HUNAN KEYUAN BIO PRODS
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