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Process for synthesizing trimethoxyphenyl stilbene

A technology of trimethoxystilbene and dimethoxybenzyl alcohol, applied in the field of environment-friendly synthesis, can solve the problems of low yield and the like, and achieve the effects of low unit consumption, less pollution of three wastes, and easy availability of raw materials

Active Publication Date: 2012-08-01
浙江新赛科药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is simple, but the yield is low

Method used

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  • Process for synthesizing trimethoxyphenyl stilbene
  • Process for synthesizing trimethoxyphenyl stilbene
  • Process for synthesizing trimethoxyphenyl stilbene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Add 84 grams of 3,5-dimethoxybenzyl alcohol (0.5mol), 150 milliliters of toluene and 73 grams of DMF (1mol) in a 500 milliliter three-necked flask, and cool to 10°C; 59.4 grams (0.2mol) of triphosgene are dissolved in Add 150 ml of toluene dropwise. During the dropwise addition, control the temperature below 15°C. After the dropwise addition, remove the ice-water bath and continue the reaction for 1 hour; let stand to separate the darker oil phase in the lower layer, and use a small amount of ice water in the upper toluene phase. and saturated sodium bicarbonate (30 ml each) were washed successively, and then concentrated to recover toluene to obtain 92.5 g of crude product.

[0053] The crude product is compared with the 3,5-dimethoxybenzyl chloride reference substance, and the HPLC peak position and the TLC spot position are consistent, indicating that the crude product is a crude product of 3,5-dimethoxybenzyl chloride.

[0054] TLC conditions: petroleum mystery: chl...

Embodiment 2

[0064] Add 92.5 grams of the crude product in Example 1 into 93 grams (0.75mol) of trimethyl phosphite and reflux for 10 hours until the oil bath temperature is 160°C ± 5°C and the internal temperature is 150°C. TLC detects that the reaction is complete and the product a is obtained .

[0065] The product a is compared with 3,5-dimethoxybenzyl phosphonic acid dimethyl ester, and the TLC spot position is consistent, indicating that the product a is 3,5-dimethoxybenzyl phosphonic acid dimethyl ester.

[0066] TLC conditions: Petroleum: chloroform: ethyl acetate = 1:1:0.1, volume ratio.

Embodiment 3

[0068] At room temperature, the product a in Example 2 was added to a methanol solution of 144.64 grams of sodium methoxide (wherein, the mass percent concentration of sodium methoxide was 28%, which was 0.75mol), stirred for 2 hours, and 68 grams of anisaldehyde ( 0.5mol), stirred at room temperature for 8 hours, heated to 80°C to recover most of methanol, and then distilled off residual methanol under reduced pressure. Be cooled to below 15 ℃, add dropwise 150 milliliters of volume percent concentration be the sulfuric acid aqueous solution of 25%, separate out product 128 grams, use 125 milliliters of volume percent concentration as the ethanol aqueous solution recrystallization of 95% to obtain 116.7 grams of white powder, yield 91 % (calculated as 3,5-dimethoxybenzyl alcohol), the purity is 99.2%.

[0069] The characterization data of the white powder are as follows: m.p.54°C-56°C, IR (cm -1 ): 3060, 1595, 1512, 1458, 1252, 1153, 961; m / z: 270, 255, 239, 147, 135, 90;

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Abstract

The invention discloses a process for synthesizing trimethoxyphenyl stilbene, which includes subjecting 3, 5-dimethoxybenzyl alcohol to chloro by triphosgene to obtain 3,5-dimethoxybenzyl chloride in a high selectivity mode, then subjecting the 3,5-dimethoxybenzyl chloride and trimethyl phosphate to reaction to obtain phosphonate, then subjecting the phosphonate and anisic aldehyde to condensation under the action of sodium methoxide to obtain 3, 4', 5- trimethoxyphenyl stilbene. The yield of crude products can reach around 95%, and the yield of synthetical pure products is above 90%. According to the process for synthesizing the trimethoxy phenyl stilbene, all materials can be fully used, and the discharging of three wastes is low; the process for synthesizing the trimethoxy phenyl stilbene is environment-friendly in producing process and has the advantages of high conversion ratio, high selectivity, easiness in obtaining raw materials and recycling auxiliary raw materials, little in three waste pollution and suitable for industrial production. The 3, 4', 5- trimethoxy phenyl stilbene can be used as a key intermediate for synthesizing trans-resveratrol.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to an environmentally friendly synthesis method of 3,4',5-trimethoxystilbene, a key intermediate of resveratrol. Background technique [0002] 3,4', 5-trimethoxystilbene is a key intermediate for the synthesis of resveratrol, for example, the US Patent No. 7253324 and the Chinese patent application whose publication number is CN101033172A describe the synthesis of resveratrol with this intermediate Methods. [0003] Resveratrol, structural formula as formula I, alias polydatin, English name: Resveratrol, chemical name: (E)-5-[2-(4-hydroxyphenyl)-vinyl]-1,3-benzenedi Phenol, 3,5,4″-trihydroxystilbene, stilbene triphenol, trans-3,5,4′-trihydroxystilbene (Trans-3,5,4′-trihydroxystilbene), molecular formula: C 14 h 12 o 3 , molecular weight: 228.25, CAS number: 501-36-0, is an anthraquinone terpenoid compound, mainly derived from the rhizome extract of Polygonum cuspidatum Sieb.et ...

Claims

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Application Information

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IPC IPC(8): C07C43/215C07C41/30C07C39/21C07C37/055
Inventor 李洪武张小兵杨和军
Owner 浙江新赛科药业有限公司
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