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Preparation method of ethyl 6,8-dichlorocaprylate

A technology of dichlorooctanoic acid ethyl ester and dichlorooctanoyl chloride, which is applied in the field of preparation of 6,8-dichlorooctanoic acid ethyl ester, can solve the problems of not ideal synthetic route, difficult control, heavy pollution, etc., and achieve safe and efficient synthetic route. Inexpensive and pollution-reducing effect

Inactive Publication Date: 2018-02-09
福安药业集团烟台只楚药业有限公司
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  • Application Information

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Problems solved by technology

[0005] Ethyl 6,8-dichlorooctanoate is an important intermediate for the preparation of lipoic acid. At present, the method for preparing ethyl 6,8-dichlorooctanoate mainly adopts the method of monoethyl adipate. The raw material of this process is monoethyl adipate The price is more expensive, and at the same time, ethylene with a very low boiling point must be used, which is not safe and difficult to control. In addition, it has to go through multi-step chlorination and the pollution is serious, so it is not an ideal synthetic route.

Method used

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  • Preparation method of ethyl 6,8-dichlorocaprylate
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  • Preparation method of ethyl 6,8-dichlorocaprylate

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Embodiment 1

[0024] In Example 1 of the present invention, a preparation method of ethyl 6,8-dichlorooctanoate specifically comprises the following steps:

[0025] 1. Mix formula (1) cyclohexanone and formula (2) vinyl ether and obtain formula (3) 2-(2'-ethoxyethyl) cyclohexanone through free radical addition, the reaction process is as follows Described in formula (I):

[0026]

[0027] ②, the formula (3) 2-(2'-ethoxyethyl) cyclohexanone is oxidized, hydrolyzed and acidified to obtain the formula (4) 8-ethoxy-6-hydroxyl-octanoic acid, the reaction process As described in formula (II):

[0028]

[0029] 3. Formula (4) 8-ethoxyl-6-hydroxyl-octanoic acid is reacted to obtain formula (5) 6,8-dihydroxyoctanoic acid through deethoxylation, and its reaction process is as described in formula (Ⅲ):

[0030]

[0031] 4., formula (5) 6,8-dihydroxyoctanoic acid is obtained through chlorination formula (6) 6,8-dichlorooctanoyl chloride, and its reaction process is as described in formula (Ⅳ...

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Abstract

The invention discloses a preparation method of ethyl 6,8-dichlorocaprylate. The preparation method is characterized in that cyclohexanone and vinyl ether which are cheap in price are mainly taken asbasic raw materials; the basic raw materials are then subjected to free-radical addition, so that 2-(2'-ethoxyethyl)cyclohexanone is obtained; secondly, the 2-(2'-ethoxyethyl)clohexanone is subjectedto oxidation, hydrolysis and acidification reaction, so that 8-ethoxyl-6-hydroxyl-octanoic acid is obtained. The synthetic raw materials adopted by the preparation method are low in whole price, and the synthesis method is simple; the step of chlorination can be effectively omitted at the same time, so that pollution is reduced; furthermore, the overall synthetic route is safe, and major safety accidents are avoided; therefore, the preparation method provided by the invention has the advantages of being economical, reasonable, safe and free from pollution.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of ethyl 6,8-dichlorooctanoate. Background technique [0002] Lipoic acid is a coenzyme found in mitochondria, similar to vitamins, which can eliminate free radicals that lead to accelerated aging and disease. Alpha lipoic acid enters the cells after being absorbed by the intestines in the body, and has both fat-soluble and water-soluble properties. [0003] Lipoic acid belongs to a class of compounds in B vitamins, a growth factor for yeast and some microorganisms, and acts as a coenzyme in a multi-enzyme system, catalyzing the oxidative decarboxylation of pyruvate into acetic acid and the oxidative decarboxylation of α-ketoglutarate into succinic acid Transacyl effect. [0004] As a coenzyme, lipoic acid plays a role in two key oxidative decarboxylation reactions, that is, in the pyruvate dehydrogenase complex and the α-ketoglutarate dehydrogenase comple...

Claims

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Application Information

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IPC IPC(8): C07C67/14C07C69/63
CPCC07C45/68C07C51/02C07C51/367C07C51/60C07C67/14
Inventor 张晓亮张家宽李东科孙晓晴刘永贵
Owner 福安药业集团烟台只楚药业有限公司
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