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Method for synthesizing aryl acetic acid through direct carbonylation of alkyl aromatic hydrocarbon and water

A technology for alkyl aromatic hydrocarbons and aryl acetic acid, applied in the field of organic synthesis, can solve problems such as low economic efficiency and environmental impact, and achieve the effects of simple raw materials, less pollution and high product purity

Active Publication Date: 2022-08-02
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since this method uses benzyl chloride as a raw material, alkali needs to be added in the reaction to neutralize the waste acid produced, and finally the phenylacetic acid hydrochloride generated needs to be acidified to obtain the product phenylacetic acid, resulting in low economic efficiency and environmental impact. also have some influence

Method used

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  • Method for synthesizing aryl acetic acid through direct carbonylation of alkyl aromatic hydrocarbon and water
  • Method for synthesizing aryl acetic acid through direct carbonylation of alkyl aromatic hydrocarbon and water
  • Method for synthesizing aryl acetic acid through direct carbonylation of alkyl aromatic hydrocarbon and water

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Preparation of phenylacetic acid

[0050]

[0051] Nickel acetate tetrahydrate (2.5mg), n-butylbis(1-adamantyl)phosphine (3.6mg), tetrabutylammonium iodide (3.7mg), toluene (3mL), water (36uL), peroxide Di-tert-butyl (183.6uL) was added to the reaction kettle, carbon monoxide was replaced 3 times, 30 atm carbon monoxide was charged, and the reaction was stirred at 140° C. for 24 hours. After the reaction, carbon monoxide was released, and phenylacetic acid was obtained by column chromatography with a yield of 54% and a purity of 98%. 1 H NMR (400MHz, CDCl 3 ):δ7.32-7.44(m,5H),3.71(s,2H). 13 CNMR (100MHz, CDCl 3 ): δ178.3, 133.2, 129.2, 128.7, 127.3, 41.3.

Embodiment 2

[0052] Example 2: Preparation of phenylacetic acid

[0053]

[0054] Cobalt nitrate hexahydrate (2.9mg), n-butylbis(1-adamantyl)phosphine (3.6mg), tetrabutylammonium iodide (3.7mg), toluene (3mL), water (36uL), peroxide Di-tert-butyl (183.6uL) was added to the reaction kettle, carbon monoxide was replaced 3 times, 30 atm carbon monoxide was charged, and the reaction was stirred at 140° C. for 24 hours. After the reaction, carbon monoxide was released, and phenylacetic acid was obtained by column chromatography with a yield of 31% and a purity of 97%.

[0055] 1 H NMR (400MHz, CDCl 3 ):δ7.32-7.44(m,5H),3.71(s,2H). 13 C NMR (100MHz, CDCl 3 ): δ178.3, 133.2, 129.2, 128.7, 127.3, 41.3.

Embodiment 3

[0056] Example 3: Preparation of phenylacetic acid

[0057]

[0058] Nickel iodide (3.1 mg), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (4.1 mg), tetrabutylammonium iodide (3.7 mg), toluene (3 mL), Water (36uL) and di-tert-butyl peroxide (183.6uL) were added to the reaction kettle, carbon monoxide was replaced 3 times, 30 atm carbon monoxide was charged, and the mixture was stirred at 140° C. for 24 hours. After the reaction, carbon monoxide was released, and phenylacetic acid was obtained by column chromatography with a yield of 63% and a purity of 96%.

[0059] 1 H NMR (400MHz, CDCl 3 ):δ7.32-7.44(m,5H),3.71(s,2H). 13 C NMR (100MHz, CDCl 3 ): δ178.3, 133.2, 129.2, 128.7, 127.3, 41.3.

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Abstract

The invention provides a method for synthesizing aryl acetic acid by direct carbonylation of alkyl aromatic hydrocarbon and water, which comprises the following steps: reacting alkyl aromatic hydrocarbon as shown in a formula I, carbon monoxide and water as raw materials under the action of a transition metal catalyst, a ligand, a phase transfer catalyst and an oxidizing agent to prepare aryl acetic acid as shown in a formula II by a one-step method. According to the method, toluene compounds and water can be directly converted into phenylacetic acid compounds in one step, additional steps such as hydrolysis and acidification are not needed, pollution is little, and the method is environmentally friendly. Meanwhile, water and toluene compounds are directly used as reactants, and the raw materials are simple, cheap and easy to obtain. The cheap transition metal compound is used as the catalyst, so that the price is low and the cost is lower. The reaction by-products are few and are greatly different from the properties of the product, the post-treatment is simple, the product is very easy to separate, and the product purity is high.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing arylacetic acid by direct carbonylation of alkyl aromatic hydrocarbons and water. Background technique [0002] Phenylacetic acid is an important synthetic intermediate, which is widely used in medicine, pesticide, fragrance and other industries. With the continuous development of these industries, the demand for phenylacetic acid is also increasing. [0003] In the pharmaceutical industry, phenylacetic acid is widely used in the preparation of penicillin. With the rapid development of penicillin and downstream product industries, the demand for phenylacetic acid is increasing. In addition, phenylacetic acid can also be used to prepare the sex hormone drug testosterone phenylacetate and the anti-ventricular arrhythmia drug Chlorkerit. Phenylacetic acid with different substituents is also widely used. For example, o-chlorophenylacetic acid can...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/08C07C51/145C07C57/32C07C57/30C07C59/64C07C57/58C07C57/40C07C201/12C07C205/56
CPCC07B41/08C07C51/145C07C201/12C07C57/32C07C57/30C07C59/64C07C57/58C07C57/40C07C205/56Y02P20/584
Inventor 黄汉民丁永正
Owner UNIV OF SCI & TECH OF CHINA
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