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Method for synthesizing 2-(3-nitrophenylmethylene)-cyclopentanone

A technology of nitrobenzylidene and nitrobenzaldehyde, applied in the field of organic chemical preparation, can solve the problems of unsustainable development, difficult separation of reaction products, low selectivity, etc., to improve cleaning and safety , Reduce the cost of the reaction process, reduce the effect of environmental pollution

Inactive Publication Date: 2013-10-09
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The organic base is used as a catalyst to prepare 2-(3-nitrobenzylidene) cyclopentanone. The reaction speed is relatively fast, but there are the following disadvantages: (1) a large amount of organic base or organic salt waste will be formed after the reaction, which needs to be recycled or processed ; (2) low selectivity, difficult separation of reaction products; (3) many wastes, unfriendly environment
Sodium hydroxide is used as a catalyst to prepare 2-(3-nitrobenzylidene) cyclopentanone. Although the environmental problem is solved, its disadvantage is that the reaction time is long, and there are many by-products, and the selectivity is not high
[0004] With the development of environmental economy, the disadvantages of unsustainable development exposed by the traditional production method of 2-(3-nitrobenzylidene) cyclopentanone urgently need to be replaced by more environmentally friendly methods. replace

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] In a 50 mL three-neck flask, add 1.05 g of cyclopentanone and 0.42 g of sodium hydroxide supported on alumina, and after magnetic stirring at 20°C for 0.5 h, add 5 ml of dimethyl sulfoxide and 1.13 g of m-nitrobenzaldehyde, continue Stir magnetically and react at 20°C for 20h. The mixture was filtered through a glass funnel to remove the catalyst. The filtrate was washed with saturated sodium bicarbonate, the organic phase was evaporated in vacuo, analyzed by gas chromatography, and the content of each component was calculated by the internal standard method. The remaining organic phase was purified by recrystallization from ethanol, dried and weighed. The conversion rate of m-nitrobenzaldehyde was 77%, the mass of 2-(3-nitrobenzylidene)-cyclopentanone was 1.61 g, and the yield was 74%.

Embodiment 2

[0026] In a 50 mL three-neck flask, add 1.05 g of cyclopentanone and 0.32 g of potassium hydroxide supported on alumina, and after magnetic stirring at 20°C for 0.5 h, add 5 ml of dimethyl sulfoxide and 0.38 g of m-nitrobenzaldehyde, continue Stir magnetically and react at 40°C for 10h. The mixture was filtered through a glass funnel to remove the catalyst. The filtrate was washed with saturated sodium bicarbonate, the organic phase was evaporated in vacuo, analyzed by gas chromatography, and the content of each component was calculated by the internal standard method. The remaining organic phase was purified by recrystallization from ethanol, dried and weighed. The conversion rate of m-nitrobenzaldehyde was 81%, the mass of 2-(3-nitrobenzylidene)-cyclopentanone was 1.77 g, and the yield was 81%.

Embodiment 3

[0028] In a 50 mL three-necked flask, add 1.05 g of cyclopentanone and 0.32 g of potassium hydroxide supported on alumina, and after magnetic stirring at 20°C for 0.5 h, add 5 ml of dimethyl sulfoxide and 2.27 g of m-nitrobenzaldehyde, continue Stir magnetically and react at 70°C for 10h. The mixture was filtered through a glass funnel to remove the catalyst. The filtrate was washed with saturated sodium bicarbonate, the organic phase was evaporated in vacuo, analyzed by gas chromatography, and the content of each component was calculated by the internal standard method. The remaining organic phase was purified by recrystallization from ethanol, dried and weighed. The conversion rate of m-nitrobenzaldehyde was 86%, the mass of 2-(3-nitrobenzylidene)-cyclopentanone was 1.94 g, and the yield was 89%.

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Abstract

The invention discloses a method for synthesizing 2-(3-nitrophenylmethylene)-cyclopentanone. The method comprises the following steps: adding cyclopentanone and alumina-supported inorganic alkali catalyst into a reactor, and sufficiently stirring to react; adding solvent and nitrobenzaldehyde into the reactor to continue the reaction; and after the reaction finishes, purifying by recrystallization. The alumina-supported inorganic alkali is used as the catalyst instead of the organic alkali catalyst, thereby enhancing the atom utilization ratio of the reaction, avoiding using high-toxicity precursor reagents in the traditional synthesis method, enhancing the cleanness in industrial synthetic reaction, and lowering the environmental pollution; the invention does not have waste acid treatment or no strong acid corrosivity, and thus, has the advantages of saving energy, reducing emission and being high in safety; the reaction can be completed at room temperature under atmospheric pressure.

Description

technical field [0001] The present invention relates to a method for synthesizing 2-(3-nitrobenzylidene)cyclopentanone, in particular to a method for synthesizing 2-(3-nitrobenzylidene)cyclopentanone with alumina-loaded inorganic base as catalyst and cyclopentanone and m-nitrobenzaldehyde as raw materials A method for 2-(3-nitrobenzylidene)cyclopentanone belongs to the field of organic chemical preparation. Background technique [0002] 2-(3-Nitrobenzylidene)cyclopentanone is an important chemical intermediate, which can be used to further produce polymers such as spices, medicines, plastics, rubber additives, or to manufacture detergents, plasticizers, etc. [0003] The industrial production of 2-(3-nitrobenzylidene) cyclopentanone at home and abroad is mainly based on cyclopentanone and m-nitrobenzaldehyde as raw materials and prepared under the conditions of using sodium hydroxide or an organic base as a catalyst. The organic base is used as a catalyst to prepare 2-(3-ni...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/45
Inventor 彭新华赵婧如马庆国邢婉贞
Owner NANJING UNIV OF SCI & TECH
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