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Method for synthesizing veratric alcohol

A synthesis method and technology of resveratrol are applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve the problems of difficult conversion, harsh reaction conditions, waste of solvents and products, etc. The effect of mild reaction conditions and cost reduction

Inactive Publication Date: 2007-02-07
JINAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] This document adopts the wittig reaction, which has certain disadvantages: the reaction conditions are relatively harsh, the reaction temperature is low, and anhydrous conditions are required; when the product II is prepared, the by-products generated are not easily soluble in water, which brings difficulties to product purification. Column chromatography is used for purification, resulting in a large waste of solvents and products; when preparing product III, the cis-trans mixture II is obtained first, and further isomerization is required, and the conversion is relatively difficult; using BB 3 Deprotection group, the dosage is relatively large, and the price is relatively expensive, unstable to light, heat and water, and inconvenient to operate

Method used

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  • Method for synthesizing veratric alcohol
  • Method for synthesizing veratric alcohol
  • Method for synthesizing veratric alcohol

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Embodiment 1

[0023] Step A: Take 20g of p-methoxybenzyl alcohol and 100ml of benzene in a three-necked round bottom flask equipped with a condenser, stir, water bath, and evenly and quickly introduce HBr gas, and the solution will change from turbidity to transparent, and then heat to 58℃ , React for about 0.5 hours, wash 300ml×4 with water, use anhydrous MgSO for organic phase 4 After drying and rotary evaporation to remove benzene, 20.81 g of p-methoxybenzyl bromide was obtained as a yellow oil (yield 71.4%), which was directly used in the next reaction.

[0024] Step B: 19.75g of p-methoxybenzyl bromide (unpurified) is reacted with 56ml of triethyl phosphite at 90-100°C for 3 hours, and the triethyl phosphite is removed under reduced pressure by rotating to obtain p-methoxybenzyl 36.98g of diethyl phosphate was directly used in the next reaction.

[0025] Step C: 36.98g p-methoxybenzyl diethyl phosphate (unpurified) was placed in 250ml dry DMF, cooled to below 0°C in an ice bath, stirred qu...

Embodiment 2

[0028] Step A: Take 20g of p-methoxybenzyl alcohol and 100ml of benzene in a three-necked round bottom flask equipped with a condenser, stir, water bath, and evenly and quickly introduce HBr gas, the solution can be changed from turbid to transparent, and then heated to 50°C , React for about 1 hour, wash 300ml×4 with water, use anhydrous MgSO for organic phase 4 After drying, the benzene was removed by rotary evaporation to obtain p-methoxybenzyl bromide as a yellow oil, which was directly used in the next reaction.

[0029] Step B: 19.75g of p-methoxybenzyl bromide (unpurified) is reacted with 56ml of triethyl phosphite at 90-100°C for 2h, and the triethyl phosphite is removed under reduced pressure by rotating to obtain p-methoxybenzyl 35.08g of diethyl phosphate was used directly in the next reaction.

[0030] Step C: 36.98g p-methoxybenzyl diethyl phosphate (unpurified) was placed in 250ml dry DMF, cooled to below 0°C in an ice bath, stirred quickly, and added 24.55g NaOCH 3 ...

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Abstract

The invention discloses a synthesis method for resveratrol, including (1) discharging hydrogen bromide gas to benzene solution of p-methoxy benzyl alcohol to obtain p-methoxy benzyl bromide, (2) carrying out reaction of p-benzyl bromide with triethyl phosphate to obtain diethyl p-methoxy benzyl phosphate, (3) carrying out reaction of diethyl p-methoxy benzyl phosphate with sodium amide and 3,5-dimethoxybenzaldehyde to obtain (E)-3, 4', 5-trimethoxystilbene, and (4) carrying out reaction of (E)-3, 4', 5- trimethoxystilbene with aluminum iodide to obtain the final product. The invention has the advantages of raw materials easy to get, lowered cost, mild reaction conditions, simplified operation, and enhanced yield.

Description

technical field [0001] The invention relates to a synthesis method of functional food ingredient resveratrol. technical background [0002] The chemical name of the compound resveratrol (Resveratrol) is (E)-3,4',5-trihydroxystilbene, which is a non-flavonoid polyphenol compound containing a stilbene structure, and has obvious antioxidant and anti The function of free radicals and delaying the aging of human body functions has significant pharmacological activities of anti-cancer, anti-inflammatory, bactericidal, blood-lipid-lowering, anti-thrombotic, anti-atherosclerosis, and prevention of cardiovascular and cerebrovascular diseases. It can be widely used in health care products, medicine, Cosmetics and other fields, in food applications, can be used as functional food ingredients. The structure of this compound is as follows: [0003] [0004] The synthesis methods reported in literature mainly include Wittig method and Heck method. The reaction conditions of the Witt...

Claims

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Application Information

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IPC IPC(8): C07C39/205C07C37/20
Inventor 晏日安丁刘刚冯锦玲傅玉萍
Owner JINAN UNIVERSITY
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