Synthesis method of 8-chloro ethyl caprylate

A technology of ethyl chlorooctanoate and a synthesis method, which is applied in the preparation of carboxylate, chemical instruments and methods, preparation of carboxylate, etc., can solve the problems of low yield, many side reactions, unsuitable for industrial production and the like, and achieves purity high effect

Pending Publication Date: 2021-02-26
安徽昊帆生物有限公司
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Problems solved by technology

[0007] Yet, 1,6-dichlorohexane reacts with diethyl malonate to synthesize 2-(6-chlorohexyl) diethyl malonate process is easy to produce multi-substituted impurities, resulting in low yield, and 2- (6-Chlorohexyl) diethyl malonate and sulfuric acid high-temperature decarboxylation process have more side reactions so that this route is not suitable for industrial production

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  • Synthesis method of 8-chloro ethyl caprylate
  • Synthesis method of 8-chloro ethyl caprylate
  • Synthesis method of 8-chloro ethyl caprylate

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preparation example Construction

[0028] According to the synthetic method of the 8-chlorooctanoic acid ethyl ester of the embodiment of the present invention, comprise the steps:

[0029] Step S1, chlorinating 1,8-octanediol with a chlorination reagent in an aromatic hydrocarbon solvent to obtain 8-chloro-1-octanol.

[0030] Specifically, its chemical reaction formula is shown in the following formula (3):

[0031]

[0032] According to the synthesis method of ethyl 8-chlorooctanoate in the embodiment of the present invention, 1,8-octanediol is used as a raw material, and the raw material is easy to obtain and low in price.

[0033] In addition, in the step S1, the aromatic hydrocarbon solvent is one or more selected from benzene, toluene, and xylene, and the chlorination reagent is selected from phosphorus trichloride, hydrochloric acid, thionyl chloride, One or more of anhydrous zinc chloride and chlorine gas. The raw material 1,8-octanediol used in the present invention can be well dissolved in these ...

Embodiment 1

[0057] Pour the raw material 1,8-octanediol (80g, 1.0eq), 30% hydrochloric acid solution (599g 9.0eq) and solvent toluene (200mL) into the reaction bottle, start stirring, raise the temperature for reflux reaction, control the reaction temperature at 102-115 Celsius, and continued to react for 10 h after heating up to reflux state.

[0058] After the completion of the reaction detected by central control GC, the water layer was separated, the organic layer was washed with water and dried, and the solvent was removed under reduced pressure to obtain the crude compound. The crude product was purified by vacuum distillation to obtain 70.2 g of the compound 8-chloro-1-octanol, the fraction temperature was 56-63 degrees Celsius, and the yield was 78%.

[0059] Pour the compound 8-chloro-1-octanol (60g 1.0eq) and the solvent dichloromethane (270mL) into the reaction flask, start stirring, add sodium hypochlorite (81.3g, 3.0eq) in batches, control the reaction temperature 45-55 degr...

Embodiment 2

[0063] Pour the raw material 1,8-octanediol (2kg, 1.0eq), 30% hydrochloric acid solution (13.3kg 8.0eq) and solvent toluene (5L) into the reaction bottle, start stirring, heat up for reflux reaction, control the reaction temperature 103~ 113 degrees Celsius, after heating up to the reflux state, the reaction was continued for 12 hours.

[0064] The central control GC detects that the reaction is complete, and the water layer is separated. The organic layer is washed and dried, and the solvent is removed under reduced pressure to obtain the crude product of compound 8-chloro-1-octanol. The crude product is purified by distillation under reduced pressure to obtain the compound 8-chloro-1-octanol Alcohol 1824g, distillate temperature 56~63 degrees centigrade, yield 81%.

[0065] Pour the compound 8-chloro-1-octanol (1824g 1.0eq) and the solvent dichloromethane (8200mL) into the reaction flask, start stirring, put in the raw material sodium hypochlorite (3309g 4.0eq) in batches fo...

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Abstract

The invention provides a synthesis method of 8-chloro ethyl caprylate. The synthesis method comprises the following steps: S1, carrying out chlorination reaction on 1, 8-octanediol and a chlorinationreagent in an aromatic solvent to obtain 8-chloro-1-octyl alcohol; s2, carrying out oxidation reaction on the 8-chloro-1-octyl alcohol and an oxidizing agent to obtain 8-chloro caprylic acid; and S3,carrying out esterification reaction on the 8-chloro caprylic acid and ethanol under the action of a catalyst to generate the 8-chloro ethyl caprylate. According to the synthesis method of the 8-chloro ethyl caprylate, a high-purity product can be obtained, and the method is simple, convenient, easy to treat, simple in process, capable of overcoming the defects in the prior art and suitable for achieving industrial production. According to the synthesis method of the 8-chloro ethyl caprylate, the high-purity product can be obtained, and the method is simple, convenient, easy to treat, simple in process, few in side reaction and suitable for industrial production.

Description

Technical field: [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing ethyl 8-chlorooctanoate. Background technique [0002] 8-Ethyl chlorooctanoate, the CAS number is 105484-55-7, and the structure is as shown in the following formula (1): [0003] [0004] 8-Chloroctanoic acid ethyl ester is an excellent solvent and an important pharmaceutical and pesticide intermediate with high development value. [0005] At present, there are few documents about the synthesis of ethyl 8-chlorooctanoate, and the existing literature mainly studies the report on the synthesis of ethyl 8-chlorooctanoate from diethyl malonate. Specifically, 1,6-dichlorohexane and diethyl malonate were used as initial raw materials, supplemented with tetramethylammonium chloride (TMAC) phase transfer catalyst, and potassium carbonate powder was used as base to synthesize 2-(6- Chlorohexyl) diethyl malonate, and then selectively react under sulfuric ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/63
CPCC07C67/08C07C51/29C07C51/305C07C29/62C07C69/63C07C53/19C07C31/36
Inventor 顾寿胜顾耿峰胡泽林
Owner 安徽昊帆生物有限公司
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