Method for preparing 2-(P-chloromethyl phenyl) propionic acid/ester

A chloromethylphenyl, propionic acid technology, applied in the preparation of carboxylate, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of high cost, many steps, etc., and achieves low equipment requirements, simple operation, high yield effect

Inactive Publication Date: 2006-04-12
XIAMEN UNIV
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  • Abstract
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  • Method for preparing 2-(P-chloromethyl phenyl) propionic acid/ester
  • Method for preparing 2-(P-chloromethyl phenyl) propionic acid/ester
  • Method for preparing 2-(P-chloromethyl phenyl) propionic acid/ester

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Embodiment 1

[0024] Add 80g of chlorobenzene, 50g (0.305mol) of 2-(p-methylphenyl)propionic acid, and 2,2′-azobisisobutyronitrile to a 250ml round bottom flask equipped with a mechanical stirrer and reflux condenser. (AIBN) 2.46g (0.015mol), then control the reaction temperature to 70°C, slowly add 45.4g (0.336mol) of sulfonyl chloride dropwise, and complete the addition within 3h. The reaction mixture was cooled to room temperature, and then continued to be cooled to 0~5°C, and filtered with suction. The solid was recrystallized with a mixed solvent of benzene and petroleum ether to obtain 44.2 g of 2-(p-chloromethylphenyl)propionic acid with a yield of 73. %, the product is white crystals, and its purity is 98% as detected by high pressure liquid chromatography. 1H NMR (500M, CDCl3, ppm): 1.5 (3H, d, J = 7.0 Hz), 3.7 (1H, q, J = 7.0 Hz), 4.7 (2H, s), 7.3 (4H, dd), 11.3 ( 1H, s, br). IR (film): 3400, 2950, ​​1700, 1420, 1220 cm-1. ESI-MS: m / z(%)=199(100) [M+H].

Embodiment 2

[0026] Add 80g of chlorobenzene and 50g (0.305mol) of 2-(p-methylphenyl)propionic acid to a 250ml round-bottomed flask equipped with a mechanical stirrer and reflux condenser. Under the mercury lamp irradiation, the reaction temperature is controlled to 48 At ℃, 45.4g (0.336mol) of sulfonyl chloride was slowly added dropwise, and the addition was completed within 3h. The reaction mixture was cooled to room temperature, then continued to be cooled to 0~5°C, and filtered with suction. The solid was recrystallized with a mixed solvent of benzene and petroleum ether to obtain 43.0g of 2-(p-chloromethylphenyl)propionic acid with a yield of 71 %.

Embodiment 3

[0028] In a 250ml round bottom flask equipped with a mechanical stirrer and reflux condenser, 80g of benzene, 50g (0.305mol) of 2-(p-methylphenyl)propionic acid, and 3.63g (0.015) of benzoyl peroxide (BPO) were added. mol), and then control the reaction temperature to 75°C, slowly add 45.4g (0.336mol) of sulfonyl chloride dropwise, and complete the addition within 3h. The reaction mixture was cooled to room temperature, then continued to be cooled to 0~5°C, filtered with suction, and the solid was recrystallized with a mixed solvent of benzene and petroleum ether to obtain 42.4 g of 2-(p-chloromethylphenyl)propionic acid, with a yield of 70 %, the product is white crystals, and its purity is 98% as detected by high pressure liquid chromatography.

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Abstract

This invention discloses a reaction thermal balance regulation method in acetic acid production process through carbonyl synthesis with methanol under low pressure and liquid phase. In the production process of acetic acid synthesized with methanol and carbon monoxide, recirculating flash distillation mother liquor which has lower temperature than reaction temperature with a recirculating mother liquor pump to balance the thermal quantity of synthesis reactor, it is characterized by setting a heat exchanger after recirculating mother liquor pump, to decrease the temperature of mother liquor from 124 DEG C ¿C 126 DEG C to 80 DEG C ¿C 110 DEG C, to balance reaction heat of reaction system through decreasing the temperature of recirculating mother liquid. Compared with the heat exchange method through outside-recirculating of reactor, the invention avoids catalyst deposits in heat exchanger under high temperature because of insufficient carbon monoxide, and avoids corrosion of recirculating pump under high temperature medium as well.

Description

Technical field [0001] The present invention relates to a method for synthesizing 2-(p-chloromethylphenyl) propionic acid or ester II, in particular to a method using 2-(p-methylphenyl) propionic acid (or ester) I as a raw material , Synthesis of 2-(p-chloromethylphenyl) propionic acid or ester II method. Background technique [0002] The structural formula of 2-(p-chloromethylphenyl)propionic acid / ester is: [0003] [0004] Wherein, R=H or -CH3 or -CH2CH3. [0005] 2-(p-chloromethylphenyl) propionic acid (or ester) is an important raw material and intermediate in the fields of agricultural chemistry, fine chemicals or pharmaceuticals (such as anti-inflammatory painkillers, etc.). The synthesis of chloromethylbenzene has been reported so far. Methods of propionic acid and its derivatives are: [0006] (1) The Japanese patent with the patent number JP No. 87-129250 provides a method for synthesizing 2-(p-chloromethylphenyl) propionic acid (or ester), that is, under the action o...

Claims

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Application Information

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IPC IPC(8): C07C67/307C07C69/612
Inventor 詹庄平杨文振
Owner XIAMEN UNIV
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