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Synthetic method of 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone

A synthesis method and cyclopropyl technology, which are applied in the fields of compounds of Group 5/15 elements of the periodic table, preparation of carbon-based compounds, chemical instruments and methods, etc. Large and other problems, to achieve the effect of low production cost, less solvent usage, and short reaction steps

Inactive Publication Date: 2016-12-07
YANCHENEG HUIHUANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses a large amount of boron trifluoride-ether, and the safety risk is more prominent

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a 250ml three-necked flask, add 21g (0.15mol) of p-chlorobenzaldehyde, add 100ml of toluene, add 20.7g (0.15mol) of diethyl phosphite, add 1.01g (0.01mol) of triethylamine, and Stir at ℃ for 6h, then add 15.13g (0.18mol) of methylcyclopropanone, add 11.70g (0.3mol) of sodium amide, and react at 30-35°C for 18h, finally add 100ml of water, separate the organic phase, add dilute Adjust the pH=2-3 with hydrochloric acid, stir for 2 hours, separate the aqueous phase and the organic phase, and distill the organic phase under reduced pressure to obtain 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone (light yellow liquid, collected 140-155℃ / 5mmHg fraction), the mass of the main fraction is 25.70g, the content is 98.3%, and the yield is 80.9%.

[0030] After chromatographic analysis, the analysis result is: GC-MS (m / z): M + : 208(10), 162(2), 139(100), 77(19), 69(24).

Embodiment 2

[0032] In a 250ml three-necked flask, add 21g (0.15mol) of p-chlorobenzaldehyde, add 100ml of methylcyclohexane, add 20.7g (0.15mol) of diethyl phosphite, add 1.01g (0.01mol) of triethylamine, and Stir at 40-45°C for 6h, then add 15.13g (0.18mol) of methylcyclopropanone, add 33.66g (0.3mol) of potassium tert-butoxide, and react at 30-35°C for 18h, finally add 100ml of water, and separate the organic phase , add dilute hydrochloric acid to the organic phase to adjust the pH=2-3, stir for 2 hours, separate the aqueous phase and the organic phase, and distill the organic phase under reduced pressure to obtain 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone (Pale yellow liquid, collect 140-155°C / 5mmHg fraction), the mass of the main fraction is 24.15g, the content is 97.9%, and the yield is 75.8%.

Embodiment 3

[0034] In a 250ml three-necked flask, add 21g (0.15mol) of p-chlorobenzaldehyde, add 100ml of dichloromethane, add 20.7g (0.15mol) of diethyl phosphite, add 1.01g (0.01mol) of triethylamine, and Stir at -25°C for 6h, then add 15.13g (0.18mol) of methylcyclopropanone, add 16.2g (0.3mol) of sodium methoxide, and react at 20-25°C for 18h, finally add 100ml of water, separate the organic phase, and in the organic phase Add dilute hydrochloric acid to adjust the pH=2-3, stir for 2 hours, separate the aqueous phase and the organic phase, and distill the organic phase under reduced pressure to obtain 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone (light yellow liquid , collecting fractions at 140-155°C / 5mmHg), the mass of the main fraction was 23.21g, the content was 98.0%, and the yield was 72.9%.

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PUM

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Abstract

The invention relates to a synthetic method of 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone. The synthetic method comprises the following specific steps: (1) dissolving p-chlorobenzaldehyde in an organic solvent, adding dialkyl phosphate, adding base at a certain temperature to carry out a catalytic reaction for a period of time; (2) continuously adding base after the catalytic reaction, dropwise adding cyclopropyl methyl ketone within a certain temperature range, reacting for a period of time, postprocessing, and distilling to obtain high-purity 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone. The reaction equation is as shown in the specification. The method has the following advantages: the reaction steps are short; utilization rate of equipment is high; application amount of a solvent is small; production cost is low; the method is safe and environment friendly and is convenient to operate; the postprocessing mode is simple; purification is easy; and through distillation, 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone with content being 97% and above is obtained.

Description

technical field [0001] The invention belongs to the field of chemical industry, in particular to a kind of 1-(4-chlorophenyl)-2-cyclopropane [0002] Synthetic method of base-1-propanone. Background technique [0003] 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone is an important intermediate of the pesticide cyproconazole, 1-(4-chlorophenyl)-2-cyclopropyl- 1-Acetone molecular formula: C 12 h 13 ClO, chemical name: 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone, English name: 1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1. [0004] Structural formula: [0005] [0006] In the synthetic method of 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone, existing reports have low yield, complex production process, expensive raw materials, serious pollution, high toxicity, and dangerous problems such as high performance and low operability. [0007] Carry out catalytic reaction with p-chloropropiophenone and cyclopropyl bromide as CN103193612, catalyzer is sodium hydride, sodium amide, an...

Claims

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Application Information

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IPC IPC(8): C07C45/68C07C49/813
CPCC07C45/68C07F9/4056
Inventor 叶振君戴乙徐董建生朱峰郭建法
Owner YANCHENEG HUIHUANG CHEM
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