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Preparation method for p-phenylbutoxybenzoic acid

A technology of phenylbutoxybenzoic acid and styrenebutene, which is applied in the field of preparation of p-phenylbutoxybenzoic acid, can solve the problems of short reaction steps and pollution

Inactive Publication Date: 2019-10-22
HANGZHOU HUANGSEN BIOLOGICAL TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The reaction steps of this route are relatively short, and at the same time, a large amount of green copper ion wastewater and a large amount of magnesium salt solid waste generated by Grignard reagent will be involved in pollution problems.

Method used

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  • Preparation method for p-phenylbutoxybenzoic acid
  • Preparation method for p-phenylbutoxybenzoic acid
  • Preparation method for p-phenylbutoxybenzoic acid

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preparation example Construction

[0029] The invention provides a preparation method of p-phenylbutoxybenzoic acid, comprising the following steps:

[0030] Under nitrogen protection, halogenated benzene, 4-halogenated-1-butene, alkali, palladium-based catalyst and the first organic solvent are mixed to carry out Heck reaction to obtain 4-halogenated-1-phenylbutene;

[0031] Under nitrogen protection, after mixing the 4-halogenated-1-phenylbutene, the first catalyst and the second solvent, the nitrogen is replaced with hydrogen to carry out catalytic hydrogenation reduction to obtain 1-halogenated phenylbutane;

[0032] Mixing the 1-halogenated phenylbutane, methylparaben, an alkaline substance and a third solvent, and carrying out a substitution reaction to obtain methyl p-phenylbutoxybenzoate;

[0033] The methyl p-phenylbutoxybenzoate, the alkaline substance and the fourth solvent are mixed to carry out a hydrolysis reaction, and then the pH value is adjusted to be acidic to obtain p-phenylbutoxybenzoic aci...

Embodiment 1

[0071] Add 500mL of toluene, 56.3g (1.00eq) of chlorobenzene, 54.38g (1.20eq) of 4-chloro-1-butene, 90.9g (1.8eq), catalyst Pd (PPh) to a 1L four-necked bottle 3 ) 4 (1%), replaced with nitrogen three times, heated to 100° C., the incubation reaction was completed for 7h, and the chlorobenzene reaction was completed by GC detection (GC detection was less than 0.1%). Cool to 25°C, add 500 mL of water, filter, take the filtrate and wash it with 300 mL of water three times, take the organic phase and concentrate to obtain 79.2 g of 4-chloro-1-phenylbutene; the yield is 95%.

[0072] Add 300mL of ethanol, 300mL of water, 100g of 4-chloro-1-phenylbutene and 3g of 10% dry palladium carbon successively in the 1L four-necked flask, replace with hydrogen three times, and 0.3Bar reacts completely in 8 hours (GC detects 4-chloro-1- phenylbutene is less than 0.1%), stop the reaction, filter, and concentrate the filtrate to obtain 88.9 g of liquid, namely the product 1-chlorophenylbutane,...

Embodiment 2

[0079] Add 100mL of toluene, 157g (1.00eq) of bromobenzene, 108.66g (1.20eq) of 4-chloro-1-butene, 181g (1.8eq), catalyst Pd (PPh) to a 2L four-necked bottle 3 ) 4 (1%), replaced with nitrogen three times, heated to 90° C., the incubation reaction was completed for 8h, and the bromobenzene reaction was completed by GC detection (GC detection was less than 0.1%). Cool to 25°C, add 500 mL of water, filter, take the filtrate and wash with 300 mL of water three times, take the organic phase and concentrate to obtain 157.3 g, 4-chloro-1-phenylbutene, with a yield of 95%.

[0080]In the 1L four-necked flask, add ethanol 300mL, water 300mL, 4-chloro-1-phenylbutene 100g and 3g 5% dry palladium carbon successively, hydrogen is replaced three times, and 0.3Bar reacts completely in 8 hours (GC detects 4-chloro-1 - phenylbutene is less than 0.1%), stop the reaction, filter, and concentrate the filtrate to obtain 87 grams of liquid, namely the product 1-chlorophenylbutane, with a yield of...

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Abstract

The invention provides a preparation method for p-phenylbutoxybenzoic acid, belonging to the field of organic synthesis. According to the invention, palladium-based catalytic coupling is adopted, andthe Grignard reaction and the Friedel-Craft reaction are avoided, thereby avoiding the production of blue-green copper ion wastewater and generation of a large amount of acidic wastewater due to usageof aluminum trichloride; the preparation method of the invention is friendly to environment, simple in synthesis route and high in the yield of each step; and halogeno-benzene is used for replacing more expensive phenylmagnesium bromide and used as a starting material, so the preparation cost of p-phenylbutoxybenzoic acid is lowered. The p-phenylbutoxybenzoic acid obtained in the invention has good crystal form, high purity and good solubility. The data of embodiments of the invention show that the total yield of p-phenylbutoxybenzoic acid prepared in the invention is 60% or above, and the HPLC purity of p-phenylbutoxybenzoic acid is 99.9% or above.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of p-phenylbutoxybenzoic acid. Background technique [0002] Prankast Chinese chemical name: 4-oxo-8-(4-(4-phenylbutoxy)benzoylamino)-2-(tetrazol-5-yl)-4H-1-benzoyl Pyran; its structure is as follows: [0003] [0004] Prankast is a leukotriene receptor antagonist developed by Japan's Ono Company. It not only has good clinical effect on specific asthma, but also has good therapeutic effect on other types of bronchitis and asthma, with low toxicity and no adverse effects. reaction. p-phenylbutoxybenzoic acid is a key intermediate for multiple synthetic routes of pranlast. Hydrolysis to obtain the intermediate p-phenylbutoxy benzoic acid. The general formula of the route is as follows: [0005] [0006] R 1 For the leaving group, for how to synthesize this leaving group, there are many literatures and patents that have been reported and st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C65/21C07C17/269C07C17/354C07C22/04C07C67/31C07C69/92
CPCC07C17/269C07C17/354C07C51/09C07C67/31C07C22/04C07C69/92C07C65/21
Inventor 王伟文蒋贤波王太臣吴晓峰
Owner HANGZHOU HUANGSEN BIOLOGICAL TECH CO LTD
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