Synthetic method of 5-chloro-1-indanone

A technology of indanone and chlorophenylpropionic acid, which is applied in the field of synthesis of 5-chloro-1-indanone, can solve the problems of harsh reaction conditions, expensive catalysts, environmental pollution, etc., and achieve simple treatment, easy process, and easy-to-obtain raw materials Effect

Active Publication Date: 2015-09-16
上海博栋化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Solve the technical problems in the current synthetic methods such as relatively long routes, expensive catalysts or raw materials, harsh reaction conditions, high cost, and serious environmental pollution

Method used

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  • Synthetic method of 5-chloro-1-indanone
  • Synthetic method of 5-chloro-1-indanone
  • Synthetic method of 5-chloro-1-indanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) The preparation of m-chlorophenylpropionic acid has the following technical process:

[0030]

[0031] In a 100mL three-necked flask, add 40g of formic acid, 29g of diethylamine, m-chlorobenzaldehyde (10g, 0.071mol) and malonic acid (8.0g, 0.077mol), stir to dissolve, then heat up to 150°C, and reflux the reaction , after the reaction was complete as detected by TLC, pour it into 400mL of ice water and stir, then adjust the pH to 3-4 with concentrated hydrochloric acid, filter, and recrystallize the filter cake with ethyl acetate to obtain 10.4g of the target product, with a yield of 79.6% and a melting point of 71.5- 75.2°C.

[0032] (2) The preparation of 5-chloro-1-indanone has the following technical process:

[0033]

[0034] In a 100mL flask, add m-chlorophenylpropionic acid (9g, 0.049mol), 40mL of dichloromethane, malonyl chloride (5.6mL, 0.058mol), stir for 10min, then slowly add 9.4g of zinc chloride, react for about 2h, TLC After the completion of ...

Embodiment 2

[0036] (1) The preparation of m-chlorophenylpropionic acid has the following technical process:

[0037]

[0038] In a 100mL three-necked flask, add 40g of formic acid, 29g of diethylamine, m-chlorobenzaldehyde (10g, 0.071mol) and malonic acid (8.9g, 0.085mol), stir to dissolve, then heat up to 150°C, and reflux the reaction , after the reaction was complete as detected by TLC, pour it into 400mL of ice water and stir, then adjust the pH to 3-4 with concentrated hydrochloric acid, filter, and recrystallize the filter cake with ethyl acetate to obtain 10.8g of the target product, with a yield of 82.3% and a melting point of 71.9- 75.8°C.

[0039] (2) The preparation of 5-chloro-1-indanone has the following technical process:

[0040]

[0041] In a 100mL flask, add m-chlorophenylpropionic acid (9g, 0.049mol), 40mL of dichloromethane, malonyl chloride (5.8mL, 0.059mol), stir for 10min, then slowly add 9.7g of zinc chloride, react for about 2h, TLC After the completion of ...

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Abstract

The invention discloses a synthetic method of 5-chloro-1-indanone, and belongs to the field of organic synthesis. 3-chlorobenzaldehyde as raw material first reacts with propionic acid to prepare 3-chloro-phenylpropionic acid, which is then subjected to Friedel-Crafts acylation reaction to prepare 5-chloro-1-indanone. Organic solvents of formic acid diethylamine participate in the first step, and the reaction temperature is 20-150 DEG C. An organic solvent of methylene chloride and a catalyst of zinc chloride participate in the second step, and the reaction temperature is -10 to 80 DEG C. The synthesis process of 5-chloro-1-indanone provided by the invention is simple and easy for magnification, resolves the technical problems of in the presence of long synthetic route, expensive catalysts or raw materials, harsh reaction conditions and high cost in the current synthetic method; particularly in the environment, compared with the conventional synthetic method of 5-chloro-1-indanone process, the method provided by the invention avoids environmental pollution problem caused by strong acid and treatment of a large amount of wastewater.

Description

technical field [0001] The invention relates to a new synthesis method of 5-chloro-1-indanone, which belongs to the field of organic synthesis. Background technique [0002] 5-chloro-1-indanone, molecular formula: C 9 h 7 ClO; Molecular Weight: 166.61; CAS: 42348-86-7, is an important intermediate of DuPont’s new pesticide variety indoxacarb (common name: indoxacarb), and is also an important pharmaceutical intermediate. At present, according to literature reports, the synthesis of such compounds mainly contains the following five methods: [0003] Method A: m-chlorocinnamic acid method [0004] In this method, m-chlorocinnamic acid is used as a raw material, and m-chlorophenylpropionic acid is obtained by palladium-carbon reduction hydrogenation, m-chlorophenylpropionyl chloride is obtained by chlorination, and finally 5-chloro-2,3-dichloro-1-indene is obtained by ring closure. ketone. The synthetic route is shown below. The main disadvantage of this method is that the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/697C07C45/46
CPCC07C45/46C07C51/38C07C2602/08C07C49/697C07C57/58
Inventor 徐伟王翼詹长娟王华杨枭
Owner 上海博栋化学科技有限公司
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