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Synthesis method of cis-jasmonone

A technology of cis-jasmonone and a synthesis method, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of long synthesis process route, large amount of "three wastes" and low product yield, etc. , to achieve the effect of short process route, high reaction selectivity and conversion rate, and high product yield

Pending Publication Date: 2022-04-29
江苏宏邦化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All of the above methods have problems such as long synthetic process route, low product yield, large amount of "three wastes" and difficult treatment.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Put 125g (1mol) of 1,4-dichlorobutene and 375g of THF into the reactor, stir and raise the temperature to 20°C, slowly add 328g (1.1mol) of methylmagnesium chloride (25%THF solution) dropwise, and control the temperature at Stir the reaction at 20℃~25℃, when the content of 1,4-dichlorobutene is less than 1%, it is the end point of the reaction. Add saturated ammonium chloride solution to quench the hydrolysis, then add water to dissolve the salt, separate the organic phase, first recover the solvent THF under normal pressure (reuse), and then rectify under reduced pressure to obtain the intermediate product 1-chloro-2-pentene. The effective amount of the product is 91g, and the yield is 87.1%.

[0026] Put 57g (0.5mol) of 2,5-hexanedione and 171g of methylene bromide into the reactor, stir, add 200g (0.5mol) of 10% sodium hydroxide solution dropwise, and raise the temperature and reflux reaction after dropping to 2,5- The content of hexanedione less than 1% is the end ...

Embodiment 2

[0029] Put 125g (1mol) of 1,4-dichlorobutene and 375g of THF into the reactor, stir and raise the temperature to 20°C, slowly add 358g (1.2mol) of methylmagnesium chloride (25% THF solution) dropwise, and control the temperature at Stir the reaction at 20℃~25℃, when the content of 1,4-dichlorobutene is less than 1%, it is the end point of the reaction. Add saturated ammonium chloride solution to quench the hydrolysis, then add water to dissolve the salt, separate the organic phase, first recover the solvent THF under normal pressure (reuse), and then rectify under reduced pressure to obtain the intermediate product 1-chloro-2-pentene. The effective amount of the product is 95g, and the yield is 90.9%.

[0030] Put 114g (1mol) of 2,5-hexanedione and 342g of dibromomethane into the reactor, stir, add 400g (1mol) of 10% sodium hydroxide solution dropwise, and heat up and reflux the reaction until the 2,5-hexanedione A ketone content of less than 1% is the end point of the reacti...

Embodiment 3

[0033] Put 125g (1mol) of 1,4-dichlorobutene and 375g of THF into the reactor, stir and raise the temperature to 20°C, slowly add 388g (1.3mol) of methylmagnesium chloride (25%THF solution) dropwise, and control the temperature at Stir the reaction at 20℃~25℃, when the content of 1,4-dichlorobutene is less than 1%, it is the end point of the reaction. Add saturated ammonium chloride solution to quench the hydrolysis, then add water to dissolve the salt, separate the organic phase, first recover the solvent THF under normal pressure (reuse), and then rectify under reduced pressure to obtain the intermediate product 1-chloro-2-pentene. The effective amount of the product is 92g, and the yield is 88.1%.

[0034] Put 171g (1.5mol) of 2,5-hexanedione and 513g of methylene bromide into the reactor, stir, add 600g (1.5mol) of 10% sodium hydroxide solution dropwise, and raise the temperature and reflux reaction after dropping to 2,5- The content of hexanedione less than 1% is the end...

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Abstract

The invention discloses a synthesis method of cis-jasmone, which specifically comprises the following steps: carrying out Grignard reaction on 1, 4-dichlorobutene and methylmagnesium chloride in a THF (tetrahydrofuran) medium to obtain 1-chloro-2-pentene; the method comprises the following steps: carrying out cyclization reaction on 2, 5-hexanedione in a dibromomethane medium under a strong alkaline condition to obtain 3-methyl-2-cyclopentene-1-ketone. According to the method, 1-chloro-2-pentene and 3-methyl-2-cyclopentene-1-ketone are subjected to an addition / elimination reaction in an ethanol medium under an alkaline condition, and cis-jasmonone is obtained. Compared with other synthesis methods, the method has the advantages of short process route, high reaction selectivity and conversion rate, high product yield, low cost and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a synthesis of spices, in particular to a synthesis method of cis-jasmone. Background technique [0002] cis-jasmone, the scientific name is 3-methyl-2-(2-pentene)-2-cyclopenten-1-one, the appearance is colorless to light yellow oily liquid, slightly soluble in water, soluble in ethanol, Diethyl ether and carbon tetrachloride. Cis-jasmone naturally exists in jasmine, mint, pepper, spearmint, longevity flower, bergamot and tea, and has a well-diffusing floral fragrance and an elegant jasmine fragrance. It is mainly used as the base of jasmine flavors, widely used in jasmine-flavored daily chemical flavors, and various food flavors such as jasmine tea, strawberry, pineapple and mint flavors. [0003] The synthetic method report of cis-jasmone has multiple, as: 1, cyclopenten-2-ketone is raw material, carries out β-position sulfonation with sodium benzene sulfinate earlier...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/65C07C49/647
CPCC07C45/65C07C45/69C07C45/61C07C17/2632C07B2200/09C07C2601/10C07C49/647C07C49/687C07C49/597C07C21/04
Inventor 陈文抗
Owner 江苏宏邦化工科技有限公司
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