3,5-dihydroxyamylbenzene synthesis method

A technology of hydroxypentylbenzene and synthetic methods, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of low raw material cost, cumbersome synthesis, difficult synthesis, etc., and achieve the effect of low price and high purity

A technology of hydroxypentylbenzene and synthetic methods, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of low raw material cost, cumbersome synthesis, difficult synthesis, etc., and achieve the effect of low price and high purity

CN109928867AActive Publication Date: 2019-06-25JIANGSU JIMING PHARMA TECH
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  • 3,5-dihydroxyamylbenzene synthesis method
  • 3,5-dihydroxyamylbenzene synthesis method
  • 3,5-dihydroxyamylbenzene synthesis method

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[0075] The present invention discloses a synthetic method of 3,5-dihydroxypentylbenzene, comprising the following steps,

[0076] S1, using benzene and n-valeryl chloride as raw materials to perform Friedel-crafts acylation reaction under Lewis acid catalysis to obtain valerophenone;

[0077] S2. The valerophenone obtained in S1 is subjected to a nitration reaction with a nitrating agent to obtain 3,5-dinitrovalerophenone;

[0078] S3. Under the action of sodium borohydride and strong carboxylic acid, the 3,5-dinitrovalerophenone obtained in S2 is reduced to methylene from the carbonyl group to form 3,5-dinitropentylbenzene; ,5-Dinitropentylbenzene is reduced to 3,5-diaminopentylbenzene under the action of iron powder and ammonium chloride;

[0079] S4, diazotizing the 3,5-diaminopentylbenzene obtained in S31 under the action of sulfuric acid and sodium nitrite to form 3,5-dihydroxypentylbenzene.

[0080] The above reaction formula is as follows:

[0081]

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Abstract

The present invention provides a 3,5-dihydroxyamylbenzene synthesis method, which comprises: carrying out a Friedel-crafts acylation reaction on benzene under the catalysis of an acid to obtain valerophenone, wherein the acid is a Lewis acid; carrying out a nitrification reaction on the obtained valerophenone to obtain 3,5-dinitrovalerophenone; reducing the carbonyl into methylene, and reducing the nitro group to obtain 3,5-diaminoamylbenzene; and diazotizing the 3,5-diaminoamylbenzene to change into the hydroxy group so as to obtain the 3,5-dihydroxyamylbenzene. According to the present invention, the used raw materials are bulk chemical industry raw materials with low price and easy availability, the conditions of each reaction are relatively mild, the reactions belong to a large numberof the conventional reactions used in the chemical industry, and the final product 3,5-dihydroxyamylbenzene (Olivetol) obtained according to the process has high purity, wherein the purity can achievemore than 98.5%, and the single impurity is within 0.3%.

Description

technical field [0001] The invention relates to a new synthesis process of an important pharmaceutical intermediate 3,5-dihydroxypentylbenzene (CAS: 500-66-3), which belongs to the technical field of organic synthesis. Background technique [0002] 3, 5-dihydroxypentylbenzene (Olivetol) was first obtained by degrading lichenic acid (also known as D-usnic acid, pentyl ithenalic acid) extracted from lichen plants, and 3, 5- The yield of dihydroxypentylbenzene is very low. Since the discovery of 3,5-dihydroxypentylbenzene, there have been many reports on its synthesis. According to the raw materials, it can be divided into two categories. One is synthesized from raw materials without benzene rings, and the other is synthesized from raw materials containing benzene rings. synthesis. [0003] First, starting from raw materials that do not contain benzene rings: [0004] Mamor et al. used n-hexanal as a raw material to generate 2-octenoic acid ethyl ester through Witting reacti...

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Application Information

Patent Timeline
25 Jun 2019
Publication
CN109928867A
IPC
C07C37/05; C07C39/08
Inventors
陈剑戈; 李斌峰