1-(4-chlorophenyl)-2-cyclopropyl-1-acetone and preparation method for intermediate thereof

A technology of chlorophenyl and cyclopropyl, which is applied in the field of preparation of 1--2-cyclopropyl-1-propanone, can solve problems such as difficulty in realizing industrial production, and achieve the effect of simplifying the reaction process and reducing costs

Active Publication Date: 2008-02-20
常州沃富斯农化有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Difficult to achieve industrial production

Method used

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  • 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone and preparation method for intermediate thereof
  • 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone and preparation method for intermediate thereof
  • 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone and preparation method for intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Synthesis method of 1-(4-chlorophenyl)-2-methyl-3-buten-1-one.

[0038] Add 6.78g (0.05mol) p-chlorobenzonitrile to 45ml tetrahydrofuran solution, and cool 13.0g (0.2mol) zinc powder to 10°C. Then, 2.67g (0.02mol) of aluminum trichloride was added to the reaction mass, and the temperature rose to above 15°C. Then 10.12 g (0.075 mol) of butenyl bromide dissolved in 50 ml of tetrahydrofuran solution were added dropwise within 1.5 hours. After the addition, it was stirred for 3.5 hours at a temperature of 35-40°C. After the reaction was completed, 60ml of n-hexane was added and cooled to 0°C. Slowly add 36ml of 2M hydrochloric acid at the temperature of the reaction mass at 0°C, and stir for 10 minutes.

[0039] The layers were separated, and the organic layer was washed successively with 2M hydrochloric acid solution (2 times 35 ml), 5% sodium bicarbonate solution (2 times 35 ml), and sodium chloride solution (3 times 35 ml). Dry over anhydrous sodium sulfat...

Embodiment 2

[0041] Example 2 Synthesis method of 1-(4-chlorophenyl)-2-methyl-3-buten-1-one.

[0042] According to Example 1 of the present invention without adding aluminum trichloride, 5.94 g of 1-(4-chlorophenyl)-2-methyl-3-buten-1-one was obtained. The yield is 61%, and the content of the product is 81.5% through gas chromatography analysis.

Embodiment 3

[0043] Example 3 Synthesis method of 1-(4-chlorophenyl)-2-methyl-3-buten-1-one.

[0044] Add 27.5g (0.2mol) of p-chlorobenzonitrile and 52.0g (0.8mol) of zinc powder into 180ml of tetrahydrofuran solution, and cool the reaction mass to 10°C. Add 10.68g (0.08mol) of aluminum trichloride to the reaction mass, and the temperature rises above 25°C. Then 27.15 g (0.3 mol) of butenyl chloride dissolved in 153 ml of tetrahydrofuran solution were added dropwise within 1.5 hours. The temperature rises above 30°C. After the addition, it was stirred for 4 hours at a temperature of 35-40°C.

[0045]After the reaction was completed, 210 ml of n-hexane was added and cooled to 0°C. The reaction mass was slowly added with 160ml of 2M hydrochloric acid at a temperature of 0°C. The layers were separated, and the organic layer was washed successively with 2M hydrochloric acid solution (2 times 100 ml), 5% sodium bicarbonate solution (2 times 120 ml), and sodium chloride solution (3 times 100...

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Abstract

The invention relates to a preparation method of 1-(4-chlorphenyl)-2-cyclopropyl-1- rolactone(I) and cyclopropanation of 1-(4-chlorphenyl)-2-methyl-3-butylene-1-ketone(II); and the 1-(4-chlorphenyl)-2-methyl-3-butylene-1-ketone(II) is produced by the reaction of parachloronitrile, crotyl chloride, zinc powder in tetrahydrofuran and alchlor and alchlor can also not be applied; (II) is reacted with dibromomethane, zinc powder in organic solvent and cuprous chloride to produce 1-(4-chlorphenyl)-2-cyclopropyl-1- rolactone(I). Midbody (II) can not be separated and cleaned in the process of reaction.

Description

technical field [0001] The invention belongs to a preparation method of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone (I); the compound is an intermediate for preparing a biologically active substance. Its structural formula is: [0002] Background technique [0003] The preparation method steps of known 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone (I) are as follows: [0004] a) Reaction of p-chlorobenzaldehyde with magnesium and butenyl chloride gives 1-(4-chlorophenyl)-2-methyl-3-buten-1-ol. [0005] b) The obtained product is reacted with methylene bromide, zinc powder, and cuprous chloride, and the chemical reaction is accelerated by precise ultrasonic waves. [0006] c) 1-(4-chlorophenyl)-2-cyclopropyl-1-propanol reacts with oxalyl chloride and dimethyl sulfoxide in a dry dichloromethane solution at a reaction temperature of -78°C to obtain 1-(4-Chlorophenyl)-2-cyclopropyl-1-propanone (I) (Soviet Patent Publication No. 1718722, published on March 07, 1992). [0007...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/813C07C45/45C07C45/67
Inventor 乌斯高夫·亚历山大涅斯杰罗娃·丽丽娅雅罗文科·谢尔盖孔繁蕾孙永辉史志兵
Owner 常州沃富斯农化有限公司
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