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Method for synthesizing resveratrol

A technology of resveratrol and trimethoxydiphenylethanol, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the harsh conditions of the reaction, the difficulty of industrialization, and the low yield of the reaction. problems, to achieve the effect of moderate reaction conditions, a wide range of solvents, and simple operation

Active Publication Date: 2007-07-11
CHINA RESOURCES SAIKE PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] refer: Tetrahedron Letters 2002, 43(4), 597-598 The reaction conditions for the synthesis of resveratrol by the Heck method have high requirements for anhydrous and oxygen-free, and it is difficult to achieve a relatively high yield, and the pollution of the palladium catalyst is very serious
[0015] The more common problems in the above methods are that the yield of the reaction is not high, the conditions of the reaction are relatively harsh, and the industrialization is difficult. Another obvious shortcoming is that the cost is high.

Method used

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  • Method for synthesizing resveratrol
  • Method for synthesizing resveratrol
  • Method for synthesizing resveratrol

Examples

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Embodiment 1

[0037] Embodiment 1: prepare 3,5-dimethoxybenzylmagnesium bromide (being Grignard reagent) by 3,5-dimethoxybenzyl bromide

[0038] Add 26g (1.07mol) of polished magnesium chips and 100mL of anhydrous THF into a dry 1000mL three-necked reaction flask, start stirring, and heat to 60°C under nitrogen protection; slowly add 231g (1mol) of 3,5-dimethoxy The solution of benzyl bromide and 400mL THF was heated to reflux and stirred for 1h, then cooled; reacted in ultrasonic wave for 10min, the reaction was violent, and after the magnesium strip disappeared, it was cooled for later use.

Embodiment 2

[0039] Embodiment 2: Prepare 3,5,4'-trimethoxybenzidine by 3,5-dimethoxybenzylmagnesium bromide

[0040] In a dry 2000mL three-necked reaction flask, add 140g (1.03mol) of anisaldehyde and 40mL of anhydrous THF, cool in an ice-water bath to below 10°C; start stirring, and slowly add the 3,5-dimethoxybenzyl prepared in Example 1 Magnesium bromide THF solution, keep the temperature fluctuating within 10-15°C; after the dropwise addition, stir at room temperature for 2h. After the reaction is complete, cool in an ice bath, add ammonium chloride (30 g) and water (100 mL), and stir for 30 min; pour the reactant into 500 mL of water, and recover the solvent THF. Extracted with ethyl acetate (200 mL×3), dried with anhydrous calcium chloride, and rotary evaporated to obtain 245 g of white solid (yield 85%).

Embodiment 3

[0041] Embodiment 3: prepare 3,5,4'-trimethoxystilbene by 3,5,4,-trimethoxystilbene

[0042] Add 144g (0.5mol) of 3,5,4'-trimethoxybenzphenylethanol, 5g p-toluenesulfonic acid and 600mL anhydrous toluene into a dry 1000mL single-port reaction flask; install a reflux dehydration device; start stirring, and slowly Slowly heated to reflux; Reflux 18h. After the reaction is completed, the solvent toluene is recovered. The obtained solid was recrystallized in 95% ethanol to obtain 102 g of off-white solid (yield 76%).

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Abstract

The invention discloses a synthesizing method of veralkalcohol, which comprises the following steps: 1) reacting 3, 5-dimethoxy benzyl bromine and metal magnesium to generate 3, 5-dimethoxy benzyl magnesium bromide as Grignard reagent; 2) proceeding nucleophilic additional reaction for 3, 5-dimethoxy benzyl magnesium bromide and anisaldehyde to generate 3,5,4'-trimethoxydiphenyl alcohol; 3) dehydrating 3,5,4'-trimethoxydiphenyl alcohol to produce 3,5,4'-trimethoxydiphenyl ethane; 5) demethylating to obtain the product.

Description

Technical field: [0001] The invention relates to a new method for synthesizing resveratrol. Background technique: [0002] Resveratrol is a natural antioxidant that can reduce blood viscosity and keep blood flowing. It can also prevent the occurrence and development of cancer. Resveratrol has estrogen-like effects and can be used to treat breast cancer and other diseases . About the synthetic method bibliographical report of resveratrol have [0003] 1. Synthesis of resveratrol by Perkins reaction [0004] As early as 1941, Spath and Kromp first tried 1,3-dimethoxybenzaldehyde and sodium p-methoxybenzoate as substrates to obtain cis-condensation products through the Perkin reaction; then the cis-products were placed in methanol and hydrochloric acid After 48 hours of the mixed solution, the cis product was isomerized to obtain the trans crystal. The reaction formula is as follows [0005] [0006] refer: J. Org. Chem, 1997, 62, 4821-4826 [0007] 2. Synthesis of res...

Claims

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Application Information

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IPC IPC(8): C07C37/11C07C37/20C07C39/21
Inventor 王文峰邹江华宇宁刘宏林
Owner CHINA RESOURCES SAIKE PHARMA
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