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Preparation method of 2-heptylidene-cyclopentanon

A technology of heptylidene cyclopentanone and cyclopentanone, which is applied in the field of preparation of 2-heptylidene cyclopentanone, can solve problems such as cross-coupling difficulties, achieve high yield and improve the effect of atom utilization

Inactive Publication Date: 2015-09-16
ZHANGJIAGANG CITY ZHENFANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (3), will cause multiple reactions, resulting in difficulties in cross-coupling

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Cyclopentanone and n-heptanal are joined in the flask according to the molar ratio of 1.3:1, and in the stirring process, adding concentration is 1.5% sodium hydroxide catalyst and phase transfer catalyst, and phase transfer catalyst is β-cyclodextrin, and its consumption is cyclodextrin 9.5% of pentanone, the quality of sodium hydroxide is 10% of cyclopentanone, reacted at 50 DEG C for 10 hours, added hydrochloric acid after the end of the reaction to adjust the pH to about 6, took the water layer with toluene, then used sodium bicarbonate solution and Wash with sodium chloride solution, add a certain amount of toluene to the washed solution, stir at about 110°C until no more water is generated, after cooling, continue to wash with sodium bicarbonate solution and sodium chloride solution, and distill under reduced pressure , drying to obtain the finished product.

[0021] Column chromatographic separation and NMR characterization of the above-mentioned finished product...

Embodiment 2

[0023] Cyclopentanone and n-heptanal are joined in the flask according to the molar ratio of 1.3:1, and in the stirring process, adding concentration is 1.5% sodium hydroxide catalyst and phase transfer catalyst, and phase transfer catalyst is β-cyclodextrin, and its consumption is cyclodextrin 3% of pentanone, the quality of sodium hydroxide is 10% of cyclopentanone, reacted at 50 DEG C for 10 hours, added hydrochloric acid after the end of the reaction to adjust the pH to about 6, took the water layer with toluene, then used sodium bicarbonate solution and Wash with sodium chloride solution, add a certain amount of toluene to the washed solution, stir at about 110°C until no more water is generated, after cooling, continue to wash with sodium bicarbonate solution and sodium chloride solution, and distill under reduced pressure , drying to obtain the finished product.

[0024] Column chromatographic separation and NMR characterization of the above-mentioned finished product s...

Embodiment 3

[0026] Cyclopentanone and n-heptanal are joined in the flask according to the molar ratio of 1.3:1, and in the stirring process, adding concentration is 1.5% sodium hydroxide catalyst and phase transfer catalyst, and phase transfer catalyst is β-cyclodextrin, and its consumption is cyclodextrin 15% of pentanone, the quality of sodium hydroxide is 10% of cyclopentanone, reacted at 50 DEG C for 10 hours, added hydrochloric acid after the end of the reaction to adjust the pH to about 6, took the water layer with toluene, then used sodium bicarbonate solution and Wash with sodium chloride solution, add a certain amount of toluene to the washed solution, stir at about 110°C until no more water is generated, after cooling, continue to wash with sodium bicarbonate solution and sodium chloride solution, and distill under reduced pressure , drying to obtain the finished product.

[0027] Column chromatographic separation and NMR characterization of the above-mentioned finished product ...

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PUM

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Abstract

The invention discloses a preparation method of 2-heptylidene-cyclopentanon. According to the preparation method, in the presence of sodium hydroxide catalyst, cyclopentanone, n-heptaldehyde, and a phase transfer catalyst are reacted for 8 to 10h at 50 to 80 DEG C, pH value is adjusted to be 6 to 7, and methylbenzene is added; an obtained mixture is stirred at 100 to 120 DEG C until no more water is generated; and at last a finished product is obtained via washing and drying, wherein molar ratio of cyclopentanone to n-heptaldehyde ranges from 1:1 to 1.3:1. Beta-cyclodextrin is taken as the phase transfer catalyst, and is capable of increasing reaction rate, and promoting mixedaldol condensation.

Description

technical field [0001] The application belongs to the technical field of chemical industry, and in particular relates to a preparation method of 2-heptylene cyclopentanone. Background technique [0002] The aldol condensation reaction is the nucleophilic addition reaction of compounds containing α-hydrogen atoms such as ketones, aldehydes, and carboxylic acids under the action of acidic or basic catalysts to condense to obtain β-hydroxy ketones or aldehydes. [0003] The traditional aldol condensation reaction has the following disadvantages: [0004] (1), low stereoselectivity and regioselectivity; [0005] (2), after the dehydration reaction stops, α, β-unsaturated compounds can still further generate oligomers or polymers; [0006] (3), will cause multiple reactions, resulting in difficulty in cross-coupling. Contents of the invention [0007] The purpose of the present invention is to provide a kind of preparation method of 2-heptyl cyclopentanone, to overcome the d...

Claims

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Application Information

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IPC IPC(8): C07C49/597C07C45/74
CPCC07C45/74C07C2601/08C07C49/597
Inventor 曹爱春赵松雪郁培华
Owner ZHANGJIAGANG CITY ZHENFANG CHEM
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