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Method for synthesizing phenylacetic acid from benzyl chloride carbonyl

A benzyl chlorocarbonyl compound synthesis technology, applied in the field of benzyl chlorocarbonylation to synthesize phenylacetic acid, can solve the problems of large dosage, low recycling rate, environmental pollution, etc., and achieve low toxicity, enhanced water solubility, and excellent preparation process simple effect

Inactive Publication Date: 2011-05-11
NORTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are few reports about phase transfer catalysts at home and abroad, mainly tetrabutylammonium bromide, benzyltriethylammonium chloride, octadecyltrimethylammonium chloride, etc. Large, low recycling rate, serious environmental pollution and other shortcomings

Method used

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  • Method for synthesizing phenylacetic acid from benzyl chloride carbonyl
  • Method for synthesizing phenylacetic acid from benzyl chloride carbonyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: Synthesis and related characterization of phase transfer catalyst

[0020] Add 0.10 mol acetic acid and 0.12 mol N-(2-hydroxyethyl) ethylenediamine to a 100 ml three-necked flask, control the pressure at 26665 Pa, and gradually increase the reaction temperature to 200 °C, and about 1.8 ml (0.1 mol) of water Steam out. Then the system pressure was gradually reduced to 3333Pa, and about 1.8 ml (0.1mol) of water was distilled out during the reaction. Cooling under reduced pressure gave a pale yellow solid, and recrystallized to give a white solid, which was the imidazoline intermediate.

[0021] Add 10 mmol of imidazoline intermediate and 20 ml of DMF into a 100 ml three-necked flask, and heat up to 80°C. Under stirring, 11 mmol chloroethanol was slowly added dropwise. After the addition was completed, the reaction was continued for 5h. The solvent was evaporated, and 2-methyl-1-bis(2-hydroxyethyl)-2-imidazoline chloride was obtained by column s...

Embodiment 2

[0025] 2-Methyl-1-bis(2-hydroxyethyl)-2-imidazoline chloride as a phase transfer catalyst for synthesis of phenylacetic acid by carbonylation of benzyl chloride

[0026] Add 1 mmol 2-methyl-1-bis(2-hydroxyethyl)-2-imidazoline chloride phase transfer catalyst in a 250 ml three-necked flask, and add 5 mmol Co(PPh 3 ) 2 Cl 2 As the main catalyst, 2.5 mmol of triphenylphosphine as the co-catalyst, and 50 ml of xylene as the solvent, the reaction was carried out at normal temperature and pressure for 10 minutes. Add 50 mmol benzyl chloride, 40ml 30% NaOH solution, and react at 60°C for 24h. The organic phase was removed, and the aqueous phase was adjusted to pH=2 with 10% hydrochloric acid solution. The resulting solution is suction filtered to obtain phenylacetic acid in the form of white flaky crystals. Yield reaches 78.5%. 99% purity. NMR, mass spectrometry, infrared and elemental analysis data were consistent with the report.

Embodiment 3

[0028] 2-Methyl-1-bis(2-hydroxyethyl)-2-imidazoline chloride as a phase transfer catalyst for synthesis of phenylacetic acid by carbonylation of benzyl chloride

[0029] Similar to Example 2, the difference is that: the used phase transfer catalyst solution and 40ml of 30% NaOH solution recovered in the example were added to the prepared cobalt carbonyl catalyst, and the rest of the reaction conditions were the same. The yield of phenylacetic acid was 73.3%. 99% purity. NMR, mass spectrometry, infrared and elemental analysis data were consistent with the report.

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Abstract

The invention discloses a method for synthesizing phenylacetic acid from benzyl chloride carbonyl. Co(PPh3)2Cl2 is taken as a main catalyst, and 2-alkyl-1-di(2-ethoxyl)-2-imidazoline chloride which is shown as a structural formula (1) is taken as a phase transfer catalyst, wherein R is alkyl with 1 to 5 carbon atoms. The short-chain 2-alkyl-1-di(2-ethoxyl)-2-imidazoline chloride is taken as the phase transfer catalyst and has high biodegradability, low toxicity, enhanced water solubility, has a good corrosion inhibition effect on metal equipment, and is easy to separate compared with a long-chain phase transfer catalyst.

Description

technical field [0001] The invention relates to a method for synthesizing phenylacetic acid by benzyl chlorocarbonylation, belonging to the technical field of organic chemistry. Background technique [0002] Phenylacetic acid, as an important fine chemical product, has a wide range of uses in medicine, pesticides, spices and other industries. In the pharmaceutical industry, it is mainly used to manufacture penicillin G, followed by antiepileptic drugs, antidepressants, cardiovascular drugs and antirheumatic drugs; in agriculture, it is used to manufacture insecticides, fungicides, herbicides and Rodenticide, etc.; in the perfume industry, phenylacetic acid and its esters are used as fixatives and modifiers, and are widely used in soaps, detergents, cleaners, cosmetics, tobacco, food and other industries. With the development of pharmaceutical, pesticide, spice and other industries, the demand for phenylacetic acid will further increase. At present, there are more than ten ...

Claims

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Application Information

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IPC IPC(8): C07C57/32C07C51/10B01J31/24
Inventor 金洗郎李剑利王淑莉校大伟史真
Owner NORTHWEST UNIV
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