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Preparation method of 4-(4-phenylbutoxy) benzoic acid

A technology of phenylbutoxy and benzoic acid, applied in the field of preparation of 4-benzoic acid, can solve problems such as being unsuitable for large-scale industrial production, expensive phenylbutanol, complicated process, etc., and achieves short synthetic route and novel route. , the effect of high purity

Active Publication Date: 2020-08-28
KUNSHAN RIKITA PHARMA
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Problems solved by technology

[0011] This synthesis method includes the synthesis method of phenylbutanol, but phenylbutanol is expensive, and making phenylbutanol by oneself has many complicated processes and high cost, and is also not suitable for large-scale industrial production.

Method used

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  • Preparation method of 4-(4-phenylbutoxy) benzoic acid
  • Preparation method of 4-(4-phenylbutoxy) benzoic acid
  • Preparation method of 4-(4-phenylbutoxy) benzoic acid

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Embodiment

[0038] This example provides a preparation method of 4-(4-phenylbutoxy)benzoic acid, which is specifically carried out according to the following steps, and the compound γ-chlorobutyrophenone is prepared according to the literature method.

[0039] 1. Synthesis of compound 3a: methyl 4-(4-oxo-4-phenylbutoxy)benzoate

[0040] Weigh 9.1 grams of γ-chlorobutanone and 8.4 grams of methyl p-hydroxybenzoate, dissolve them in 100 milliliters of DMF, add 27.6 grams of potassium carbonate, stir, heat up, stir at 100°C for 5 hours, cool down, filter, and decompress the filtrate Concentrate, dissolve in dichloromethane, wash with 1N sodium hydroxide, separate the organic phase, dry over anhydrous sodium sulfate, filter and concentrate to obtain a white solid that is directly used in the next reaction.

[0041] Reaction formula:

[0042]

[0043] 2. Synthesis of compound 3b: benzyl 4-(4-oxo-4-phenylbutoxy)benzoate

[0044] According to the method in the first step, benzyl p-hydroxybe...

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Abstract

The invention relates to a preparation method of 4-(4-phenylbutoxy) benzoic acid, which specifically comprises the following steps: a, performing a reaction on gamma-chlorobutanone with p-hydroxybenzoate under the catalysis of alkali to generate a compound 3; b, performing catalytic reduction on the compound 2 to generate a compound 4; and c, hydrolyzing the compound 4 to obtain the 4-(4-phenylbutoxy) benzoic acid. According to the preparation method of the 4-(4-phenylbutoxy) benzoic acid, the adopted raw materials are low in price and easy to obtain; the method has the advantages of short synthetic route, novel route, no pollution and high yield.

Description

technical field [0001] The invention relates to the field of drug synthesis, and relates to a preparation method of 4-(4-phenylbutoxy)benzoic acid. Background technique [0002] 4-(4-Phenylbutoxy)benzoic acid (4-(4-Phenylbutoxy)benzoic acid), molecular formula: C 17 h 18 o 3 , belonging to pharmaceutical intermediates, is an important intermediate of the new anti-asthma drug Pranlukast. [0003] There are not many synthetic methods of 4-(4-phenylbutoxy)benzoic acid recorded in the literature, and the main methods are: [0004] [0005] The synthesis method has a lot of complicated steps, and the use of raw material benzene and intermediate product 4-phenyl-1-butyl bromide is highly toxic, and the simultaneous use of aluminum trichloride as a catalyst will generate a large amount of waste water, which is difficult to treat and has a high cost. [0006] Taking phenylbutanol as the synthetic method of starting raw material p-phenylbutoxybenzoic acid: [0007] [0008...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C65/21
CPCC07C67/30C07C67/317C07C51/09C07C69/92C07C65/21
Inventor 熊付超吴俊飞李林竹曹建刚
Owner KUNSHAN RIKITA PHARMA
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