Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

The preparation method of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone

A technology of chlorophenyl and cyclopropyl, which is applied in the preparation of carbon-based compounds, organic compounds, chemical instruments and methods, etc., can solve the problems of unsuitability for industrial scale production, unsafe magnesium powder reduction operation, and high cost of raw materials , to achieve the effects of low production cost, high product yield and high product purity

Active Publication Date: 2014-10-08
HUNAN CHEM RES INST
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method has high cost of raw materials and complex operation
Method for synthesizing 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone by seven-step reaction using 4-chlorophenylacetonitrile, 1-chloro-2-butene and 1,2-dibromomethane as raw materials , the reaction steps are long and the reaction yield is low
Using cyclopropyl methyl ketone, 4-chlorophenylacetonitrile and sodium hydride as raw materials, magnesium powder as a reducing agent, through condensation, hydrogenation and oxidation to obtain 1-(4-chlorophenyl)-2-cyclopropyl -The method of 1-acetone, this method magnesium powder reduction operation is unsafe, is not suitable for industrial scale production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • The preparation method of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone
  • The preparation method of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone
  • The preparation method of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 8.4g (0.1mol) of cyclopropylmethyl ketone, 2.2g (0.04mol) of potassium borohydride, 42g of methanol, and 42g of water into a 250mL three-necked flask with a stirring and reflux tube, and react at room temperature for 4h. After the reaction was finished, neutralize with 6N hydrochloric acid, extract and separate the liquids with ethyl acetate, dry the organic phase by adding anhydrous sodium sulfate, and remove the solvent to obtain 8.6g of 1-cyclopropylethanol with a purity of 99% (gas chromatography), and a yield of 99% (based on Cyclopropylmethyl ketone).

[0016] Add 8.6g of 1-cyclopropylethanol to a 100mL three-necked flask, slowly drop in 14.3g (0.12mol) of thionyl chloride at 10°C, add it in 30min, and react at 10°C for 4h. After the reaction was completed, the excess thionyl chloride and HCl were removed under reduced pressure, the reaction solution was washed twice with 20 mL of water, and dried by adding anhydrous sodium sulfate to obtain 10.3 g of 1-cyclop...

Embodiment 2

[0020] Add 8.4g (0.1mol) of cyclopropylmethyl ketone, 2.2g (0.04mol) of potassium borohydride, 21g of methanol, and 21g of water into a 100mL three-necked flask with a stirring and reflux tube, and react at room temperature for 4h. After the reaction was finished, neutralize with 6N hydrochloric acid, extract and separate the liquids with ethyl acetate, dry the organic phase by adding anhydrous sodium sulfate, and remove the solvent to obtain 8.2g of 1-cyclopropylethanol with a purity of 98% (gas chromatography) and a yield of 93.4% (based on Cyclopropylmethyl ketone).

[0021] Add 8.2g of 1-cyclopropylethanol to a 250mL three-necked flask, slowly drop in 13.1g (0.11mol) of thionyl chloride at 10°C, add it in 1h, and react at 10°C for 4h. After the reaction was completed, the excess thionyl chloride and HCl were removed under reduced pressure, the reaction solution was washed twice with 20 mL of water, and dried by adding anhydrous sodium sulfate to obtain 9.5 g of 1-cycloprop...

Embodiment 3

[0025] Add 8.4g (0.1mol) of cyclopropylmethyl ketone, 2.2g (0.04mol) of potassium borohydride, 34g of methanol, and 34g of water into a 250mL three-necked flask with a stirring and reflux tube, and react at room temperature for 4h. After the reaction was finished, neutralize with 6N hydrochloric acid, extract and separate the liquids with ethyl acetate, dry the organic phase by adding anhydrous sodium sulfate, and remove the solvent to obtain 8.4g of 1-cyclopropylethanol with a purity of 98.5% (gas chromatography) and a yield of 96.2% (based on Cyclopropylmethyl ketone).

[0026] Add 8.4g of 1-cyclopropylethanol to a 100mL three-necked flask, slowly drop in 14.3g (0.12mol) of thionyl chloride at 10°C, add it in 30min, and react at 10°C for 4h. After the reaction was over, the excess thionyl chloride and HCl were removed under reduced pressure, the reaction solution was washed twice with 20 mL of water, and dried by adding anhydrous sodium sulfate to obtain 9.9 g of 1-cycloprop...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone by taking 1-cyclopropyl chloroethane as a raw material. The raw material 1-cyclopropyl chloroethane is obtained by reducing cyclopropyl methyl ketone into 1-cyclopropyl ethanol which is further chlorinated into 1-cyclopropyl chloroethane. 1-Cyclopropyl chloroethane reacts with 4-chlorophenylacetonitrile to produce 2-(4-chlorphenyl)-3-cyclopropyl butyronitrile which is further oxidized to produce 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone (shown in the reaction formula 1). Alternatively, 1-cyclopropyl chloroethane undergoes cyanide hydrolysis to produce 1-cyclopropyl-2-methylacetonitrile which is further hydrolyzed into 2-cyclopropyl propionic acid as beginner for synthesis of 2-cyclopropylpropionyl chloride, and finally 2-cyclopropylpropionyl chloride reacts with chlorobenzene to produce 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone (see the reaction formula 2). The method has the characteristics of high product purity, high product yield, simple process, safe operation, cheap and easily-available raw materials, low production cost and applicability to industrial production.

Description

technical field [0001] The invention relates to a preparation method of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone. Background technique [0002] 1-(4-Chlorophenyl)-2-cyclopropyl-1-propanone is an organic intermediate widely used in the synthesis of fine chemicals such as pharmaceuticals. For example, it is used in the synthesis of cycloconazole, a high-efficiency and low-toxicity fungicide of triazoles. There are many ways to synthesize 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone. For example, the reaction of 4-chlorophenyl cyclopropyl methyl ketone with sodium hydride and methyl iodide to obtain 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone, cyclopropyl acetic acid chlorination to obtain cyclo Propyl acetyl chloride, and then react with chlorobenzene to obtain 4-chlorophenyl cyclopropyl methyl ketone. The raw material cost of this synthetic method is high. Synthesis of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone by Grignard reagent method. It uses allyl chloride an...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/813C07C45/32C07C45/46
Inventor 徐建兵周勇王宇毛春晖陈明
Owner HUNAN CHEM RES INST
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com