The preparation method of 4-furfurylthiopentanone-2

A technology of furfuryl thiopentanone and furfuryl mercaptan, which is applied in the field of fine chemistry, can solve the problems of high risk, high cost, unsuitability for industrial production and the like of the synthesis route, and achieves the optimization of the synthesis route, the improvement of the yield, and the guarantee of the product purity. Effect

Active Publication Date: 2022-04-12
石家庄和中科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The present invention proposes a preparation method of 4-furfurylthiopentanone-2, which solves the problems in the prior art that the synthesis route of 4-furfurylthiopentanone-2 is high in risk, high in cost and unsuitable for industrial production

Method used

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  • The preparation method of 4-furfurylthiopentanone-2

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Embodiment 1

[0040] The preparation method of 4-furfurylthiopentanone-2 comprises the following steps:

[0041] S1. Add 15L of toluene to the reaction kettle, slowly add 9.4kg of triphenylphosphine, add 3kg of chloroacetone after it dissolves, start to heat up and reflux, and GC detects that the reaction is complete.

[0042] Post-processing: the reaction solution was cooled to room temperature and suction filtered, the filtrate was recovered with toluene and used mechanically, the filter cake was washed 3 times with 3L petroleum ether, and the solid was dried to obtain the phosphorus salt.

[0043] S2. Add the phosphorus salt obtained in step S1 to the reactor, add 10L of dichloromethane to dissolve, then cool 7.8kg of 30% sodium hydroxide aqueous solution to room temperature and add it to stir, and the reaction is completed in 2 to 3 hours;

[0044] Post-processing: liquid separation, the dichloromethane phase was washed with 5 L of saturated ammonium chloride until neutral, and washed w...

Embodiment 2

[0050] The preparation method of 4-furfurylthiopentanone-2 comprises the following steps:

[0051] S1. Add 15L of toluene to the reaction kettle, slowly add 9.4kg of triphenylphosphine, add 3kg of chloroacetone after it dissolves, start to heat up and reflux, and GC detects that the reaction is complete.

[0052] Post-processing: the reaction solution was cooled to room temperature and suction filtered, the filtrate was recovered with toluene and used mechanically, the filter cake was washed 3 times with 3L petroleum ether, and the solid was dried to obtain the phosphorus salt.

[0053] S2. Add the phosphorus salt obtained in step S1 to the reactor, add 10L of dichloromethane to dissolve, then cool 7.8kg of 30% sodium hydroxide aqueous solution to room temperature and add it to stir, and the reaction is completed in 2 to 3 hours;

[0054]Post-processing: liquid separation, the dichloromethane phase was washed with 5 L of saturated ammonium chloride until neutral, and washed wi...

Embodiment 3

[0060] The preparation method of 4-furfurylthiopentanone-2 comprises the following steps:

[0061] S1. Add 15L of toluene to the reaction kettle, slowly add 9.4kg of triphenylphosphine, add 3kg of chloroacetone after it dissolves, start to heat up and reflux, and GC detects that the reaction is complete.

[0062] Post-processing: the reaction solution was cooled to room temperature and suction filtered, the filtrate was recovered with toluene and used mechanically, the filter cake was washed 3 times with 3L petroleum ether, and the solid was dried to obtain the phosphorus salt.

[0063] S2. Add the phosphorus salt obtained in step S1 to the reaction kettle, add 10L tetrahydrofuran to dissolve it, cool the system to 0°C, add 1.7kg 60% sodium hydride in batches, and stir for 2 to 3 hours until the reaction is completed;

[0064] Post-processing: Concentrate to remove tetrahydrofuran, add 10L of dichloromethane and 2L of water to the residue, separate the liquids, wash the dichlo...

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Abstract

The invention belongs to the technical field of fine chemistry, and provides a preparation method of 4-furfurylthiopentanone-2, which specifically comprises the following steps: adding raw material chloroacetone into a toluene solution of triphenylphosphine or adding triethyl phosphite , the temperature is raised and refluxed to obtain a phosphorus salt; the obtained phosphorus salt is dissolved in an organic solvent, a strong base is added, and stirred for 2 to 3 hours, the reaction is completed, and phosphorus ylide is obtained; Stir until the reaction is completed to obtain 3-pentene-2-ketone; piperidine is added to 3-pentene-2-ketone, the dichloromethane solution of furfuryl mercaptan is added dropwise, and the temperature of the system is controlled to be 35~ 40° C., after the dropwise addition, the mixture was stirred until the reaction was completed to obtain the product 4-furfurylthiopentanone-2. The invention solves the problems in the prior art that the synthesis route of 4-furfuryl pentanone-2 is high in danger, high in cost and unsuitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of fine chemistry and relates to a preparation method of 4-furfurylthiopentanone-2. Background technique [0002] Ketone flavoring compounds are important practical flavoring monomers, which are widely used in edible flavoring essences, and provide the required flavor characteristics for various convenience foods. 4-Furfurylthiopentanone-2 has a good meat It can be used as an important raw material for meat flavor. [0003] At present, the synthesis of 4-furfurylthiopentanone-2 mainly contains the following routes: [0004] 1. Grignard reaction [0005] [0006] The Grignard reaction is more dangerous, and the scale-up industrialization is limited. The oxidation yield of PCC is low and difficult to handle. [0007] 2. Methyl lithium reaction [0008] [0009] The use of methyllithium reagent is dangerous, and the yield is low, the cost is high, and it is not suitable for industrialization. [001...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/38
CPCC07D307/38
Inventor 郭军永张乱青曹彦雷
Owner 石家庄和中科技有限公司
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