Preparation method for 4- alkoxy-1,1,1- trifluoro-3- butane-2-ketone

A technology of alkoxy and butene, applied in the direction of condensation to prepare carbonyl compounds, organic chemistry, etc., can solve the problems of high molecular weight, high production cost and short reaction steps of trifluoroacetic anhydride, and achieve high reaction yield and low production cost. Low, easy-to-operate effect

Active Publication Date: 2014-10-01
HUNAN HAILI CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] One, using trifluoroacetic anhydride and vinyl ether as raw materials, using pyridine as an acid-binding agent to prepare the method for 4-ethoxy-1,1,1-trifluoro-3-buten-2-one, the reaction steps are short , the operation is simple, the yield is 83.

Method used

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  • Preparation method for 4- alkoxy-1,1,1- trifluoro-3- butane-2-ketone
  • Preparation method for 4- alkoxy-1,1,1- trifluoro-3- butane-2-ketone
  • Preparation method for 4- alkoxy-1,1,1- trifluoro-3- butane-2-ketone

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Embodiment 1

[0021] In a three-necked reaction flask equipped with stirring, a thermometer and a dropping funnel, add 450ml of toluene and 144g (1800mmol)) of pyridine in sequence, and add 102.6g of trifluoroacetic acid (900mmol)) dropwise at 0~-10°C, and the dropping time is about After 1 hour, the addition was completed. After adding 65.5g (900mmol) of vinyl ether at 0 to -10°C, 94.5g (945mmol) of phosgene was introduced into the reaction mixture at 0 to -10°C for about 4 hours. Gas chromatography monitoring after passing through phosgene, vinyl ether is less than 1%, add 220ml of water after the reaction is complete, stir for 60 minutes, separate layers, extract the water layer with 90ml of toluene, combine the organic phases, wash twice with 2*135ml of water, Dry the organic phase with anhydrous magnesium sulfate, filter, wash with 2*40ml toluene, combine the organic phases, detoluene at normal pressure, and distill under reduced pressure to obtain the product 4-ethoxy-1,1,1-trifluoro-3...

Embodiment 2

[0023] In a three-necked reaction flask equipped with stirring, a thermometer and a dropping funnel, add 450ml of dichloromethane and 220.3g (1800mmol)) of N,N-dimethylaniline in sequence, and dropwise add 102.6g of trifluoro Acetic acid (900mmol)), the dropwise addition time is about 1 hour, after the addition is completed, 105.6g (1800mmol) vinyl methyl ether is passed into the reaction mixture at 0~-10°C, and 94.5g ( 945mmol) phosgene, pass through in about 4 hours, monitor by gas chromatography after passing through phosgene, vinyl methyl ether is less than 1%, add 220ml water after the reaction is complete, stir for 60 minutes, separate layers, and extract the water layer with 90ml dichloromethane , combine the organic phases, wash twice with 2*135ml water, dry the organic phases with anhydrous magnesium sulfate, filter, wash with 2*40ml dichloromethane, combine the organic phases, remove dichloromethane at normal pressure, and distill under reduced pressure, 121.1 g of t...

Embodiment 3

[0025] In a three-necked reaction flask equipped with stirring, a thermometer and a dropping funnel, add 900ml of dichloroethane and 271.3g (1800mmol) of N,N-diethylaniline in sequence, and dropwise add 102.6g of trifluoro Acetic acid (900mmol)), the dropwise addition time is about 1 hour, after the addition is completed, 78.3g (900mmol) vinyl n-propyl ether is added at 0~-10°C, and 180.0g ( 1800mmol) phosgene, passed through in about 2 hours, gas chromatographic monitoring after passing through phosgene, vinyl n-propyl ether was less than 1%, after the reaction was complete, add 220ml water, stir for 60 minutes, separate layers, and use 90ml dichloroethyl ether for the water layer Extract with alkane, combine the organic phases, wash twice with 2*135ml water, dry the organic phase with anhydrous magnesium sulfate, filter, wash with 2*40ml dichloroethane, combine the organic phases, and remove dichloroethane under normal pressure, Distilled under reduced pressure to obtain 142...

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Abstract

The invention discloses a method for synthesizing 4-alkoxy-1,1,1-trifluoro-3-butane-2-ketone by taking trifluoroacetic acid, vinyl alkyl ether and phosgene as raw materials in the presence of a solvent and an acid-binding agent. A chemical reaction formula is as shown in the specification, wherein R is methyl, ethyl, n-propyl, isopropyl and normal-butyl. The preparation method disclosed by the invention is simple and convenient in process and simple to operate, has reaction yield of 85.6% (in terms of trifluoroacetic acid), and product purity of 98%, and is low in production cost and suitable for industrial production.

Description

technical field [0001] The present invention relates to a preparation method of 4-alkoxy-1,1,1-trifluoro-3-buten-2-one. Background technique [0002] 4-Alkoxy-1,1,1-trifluoro-3-buten-2-one is an important intermediate of pesticides and medicines, and has the following general formula: [0003] [0004] In the formula, R is methyl, ethyl, n-propyl, isopropyl and n-butyl. [0005] According to the preparation method of 4-alkoxy-1,1,1-trifluoro-3-buten-2-one reported in domestic and foreign literature at present, mainly take trifluoroacetic anhydride or trifluoroacetyl chloride as raw material, but All there is production cost higher, is unfavorable for extensive popularization and application. Such as: [0006] One, using trifluoroacetic anhydride and vinyl ether as raw materials, using pyridine as an acid-binding agent to prepare the method for 4-ethoxy-1,1,1-trifluoro-3-buten-2-one, the reaction steps are short , simple operation, 83.6% yield (calculated by trifluoroa...

Claims

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Application Information

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IPC IPC(8): C07C45/47C07C49/255
CPCC07C45/47C07C49/255
Inventor 熊莉莉杜升华黄超群罗亮明
Owner HUNAN HAILI CHEM IND
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