P-phenylbutoxy benzoic acid and preparation method thereof

A technology of p-phenylbutoxybenzoic acid and phenylbutoxybenzoic acid, which is applied in the field of preparation of pranlukast intermediate p-phenylbutoxybenzoic acid, can solve the problem of no batch production, low synthesis yield and cost Advanced problems, to achieve the effect of low equipment requirements, low price and high yield

Inactive Publication Date: 2016-07-06
叶芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the market demand for p-phenylbutoxybenzoic acid is gradually increasing, but there is no relevant report on mass production in China, and the cost of synthesis in the current synthesis method is relatively high, and the synthesis yield is relatively low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The preparation method of p-phenylbutoxybenzoic acid comprises the following steps:

[0022] (1) Add 20 mol of 1,4-dibromobutane, 2 mol of benzene, and 0.5 mol of catalyst into a three-necked flask, react at 5°C for 2 h, add 20 ml of a mixture of ice water and concentrated hydrochloric acid after the reaction, stir for 20 min, separate Organic phase, using benzene to extract the aqueous phase, the organic phases were combined, washed with deionized water, then dried, filtered, and the filtrate was distilled under reduced pressure to remove benzene and 1,4-dibromobutane to obtain 4-phenylbromobutane , the yield is 85.8%;

[0023] (2) Add 1 mol of 4-phenylbromobutane, 1 mol of methyl p-hydroxybenzoate, 0.2 mol of sodium bromide, and 0.3 mol of sodium sulfide into a three-necked flask, mix and stir evenly, react at 60°C, and cool down after the reaction is completed to room temperature, added deionized water to wash, and extracted with dichloromethane. The obtained organi...

Embodiment 2

[0026] The preparation method of pranlukast intermediate p-phenylbutoxybenzoic acid comprises the following steps:

[0027] (1) Add 20 mol of 1,4-dibromobutane, 5 mol of benzene, and 1 mol of catalyst into a three-necked flask, react at 15°C for 5 h, add 50 ml of a mixture of ice water and concentrated hydrochloric acid after the reaction, stir for 30 min, and separate the organic Phase, using benzene to extract the water phase, the organic phases were combined, washed with deionized water, then dried, filtered, and the filtrate was distilled under reduced pressure to remove benzene and 1,4-dibromobutane to obtain 4-phenylbromobutane, The yield is 93.6%;

[0028] (2) Add 2 mol of 4-phenylbromobutane, 1 mol of methyl p-hydroxybenzoate, 0.5 mol of sodium bromide, and 0.3 mol of sodium sulfide into a three-necked flask, mix and stir evenly, react at 70°C, and cool down after the reaction is completed to room temperature, added deionized water to wash, dichloromethane extracted, ...

Embodiment 3

[0031] The preparation method of pranlukast intermediate p-phenylbutoxybenzoic acid comprises the following steps:

[0032] (1) Add 20 mol of 1,4-dibromobutane, 3 mol of benzene, and 0.6 mol of catalyst into a three-necked flask, react at 10°C for 3 hours, add 30 ml of a mixture of ice water and concentrated hydrochloric acid after the reaction, stir for 25 minutes, separate Organic phase, using benzene to extract the aqueous phase, the organic phases were combined, washed with deionized water, then dried, filtered, and the filtrate was distilled under reduced pressure to remove benzene and 1,4-dibromobutane to obtain 4-phenylbromobutane , the yield is 88%;

[0033] (2) Add 1.2mol of 4-phenylbromobutane, 1mol of methyl p-hydroxybenzoate, 0.3mol of sodium bromide, and 0.3mol of sodium sulfide into a three-necked flask, mix and stir evenly, and react at 65°C. After the reaction is completed, Cool to room temperature, add deionized water to wash, extract with dichloromethane, re...

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PUM

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Abstract

The invention discloses a preparation method of p-phenylbutoxy benzoic acid. The preparation method comprises the following steps: by using 1,4-dibromobutane as a raw material, carrying out reaction on the 1,4-dibromobutane and benzene to obtain 4-phenylbromobutane; carrying out reaction on the 4-phenylbromobutane and methyl p-hydroxybenzoate to obtain methyl p-phenylbutoxy benzoate; and oxidizing the methyl p-phenylbutoxy benzoate, and meanwhile, carrying out hydrolysis to obtain the pranlukast intermediate p-phenylbutoxy benzoic acid. The p-phenylbutoxy benzoic acid prepared by the method has the advantages of high purity and high yield; and the method has the advantages of cheap and accessible raw materials, mild preparation conditions, high controllability and low production cost.

Description

Technical field: [0001] The invention relates to the technical field of biomedicine, in particular to a preparation method of pranlukast intermediate p-phenylbutoxybenzoic acid. Background technique: [0002] In recent years, the environment has deteriorated, and the number of asthma patients has increased year by year, so the prevention and control of asthma is imminent. Prankast is a leukotriene C4 / D4 receptor antagonist with low toxicity. It can selectively inhibit the activity of airway smooth muscle leukotriene polypeptides, has little effect on arachidonic acid metabolic enzymes, and has no effect on acetylcholine , 5-hydroxytryptamine, etc. have no antagonistic effect, and have significant inhibitory effects on LTC4, LTD4, LTE4, etc., especially on LTD4 (the main component that causes the contraction of human tracheal smooth muscle), which plays an important role in the occurrence, development and control of asthma Important role, no adverse reactions. Studies have ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/24C07C27/02C07C51/09
CPCC07C51/09C07C17/266C07C67/31C07C65/24C07C69/92C07C22/04
Inventor 叶芳
Owner 叶芳
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