Synthetic method of 6-hydroxy-8-chloro ethyl caprylate, 6, 8-dichloro ethyl caprylate and lipoic acid

A technology of ethyl dichlorooctanoate and ethyl chlorooctanoate, applied in the field of organic synthesis, can solve problems such as low yield, and achieve the effects of low cost, low cost and easy operation

Pending Publication Date: 2022-03-08
XIAMEN KINGDOMWAY VI TAMIN INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] One of the purposes of the present invention is to overcome the defect that the yield is lower when substrate 6-oxo-8-chlorooctanoic acid ethyl ester is reduced to 6-hy

Method used

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  • Synthetic method of 6-hydroxy-8-chloro ethyl caprylate, 6, 8-dichloro ethyl caprylate and lipoic acid
  • Synthetic method of 6-hydroxy-8-chloro ethyl caprylate, 6, 8-dichloro ethyl caprylate and lipoic acid
  • Synthetic method of 6-hydroxy-8-chloro ethyl caprylate, 6, 8-dichloro ethyl caprylate and lipoic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Under a nitrogen atmosphere at room temperature, a dichloroethane solution (150 g, 15% w / w) of 6-oxo-8-chlorooctanoic acid ethyl ester was poured into a reaction kettle with a rectifying tower, and lithium chloride (0.85 g, 0.2 equivalents), potassium phosphate (21.23 g, 1.0 equivalents) and isopropanol (38 mL, 5.0 equivalents), stirred for 10 min, heated to 83-85° C. and refluxed for 6 hours. During the reaction, the isopropanol-dichloroethane is separated from the acetone produced by the reaction through a rectification tower, and the isopropanol-dichloroethane flows back into the reactor to separate the acetone. The reaction was tracked by thin-layer chromatography. After the reaction was completed, the excess isopropanol and dichloroethane were distilled off under reduced pressure, and then the solids in the system were removed by filtration, and then the product 6-hydroxyl-8- Ethyl chlorooctanoate 19.92g, the content is 98.3%, the yield is 88.2%.

Embodiment 2-5

[0041] Synthesize 6-hydroxyl-8-chlorooctanoic acid ethyl ester according to the method of Example 1, the difference is that the amount of catalyst and the reaction time are changed according to the manner in Table 1, and the remaining conditions are the same as in Example 1 to obtain 6-hydroxyl-8-chlorooctanoic acid Ethyl esters, the results are shown in Table 1.

Embodiment 6

[0055] Embodiment 6 changes the consumption of Virahol and the reaction time

[0056] Synthesize 6-hydroxy-8-chlorooctanoic acid ethyl ester according to the method of Example 1, the difference is that the amount of isopropanol is adjusted from 5.0 equivalents to 4.0 equivalents, and the reaction time is adjusted to 10 hours, and the remaining conditions are the same as in Example 1 Same, the specific steps are as follows:

[0057] Under a nitrogen atmosphere at room temperature, a dichloroethane solution (150 g, 15% w / w) of 6-oxo-8-chlorooctanoic acid ethyl ester was poured into a reaction kettle with a rectifying tower, and lithium chloride (0.85 g, 0.2 equivalents), potassium phosphate (21.23 g, 1.0 equivalents) and isopropanol (24 mL, 4.0 equivalents), stirred for 10 min, heated to 83-85 ° C for 10 hours under reflux. During the reaction, the isopropanol-dichloroethane is separated from the acetone produced by the reaction through a rectification tower, and the isopropano...

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Abstract

The invention belongs to the field of organic synthesis, and relates to a synthesis method of 6-hydroxy-8-chloro ethyl caprylate, 6, 8-dichloro ethyl caprylate and lipoic acid. The synthesis method of 6-hydroxy-8-chloro ethyl caprylate comprises the following steps: in the presence of a catalyst, 6-oxo-8-chloro ethyl caprylate is converted into 6-hydroxy-8-chloro ethyl caprylate by adopting MPV reduction reaction, the catalyst is composed of a catalyst I and a catalyst II, the catalyst I is lithium chloride and/or lithium bromide, the catalyst II is potassium phosphate, and the catalyst II is potassium chloride and/or lithium bromide. The molar ratio of the catalyst I to the catalyst II is 1: (1-20). According to the method, the MPV reduction reaction is co-catalyzed by adopting two types of inorganic salts, namely lithium chloride/lithium bromide and potassium phosphate, so that the activity of the MPV reduction reaction can be improved, the yield of the obtained product is up to 80% or above, the limitation that the existing MPV reduction reaction condition is not suitable for a beta-position chloro carbonyl compound, namely ethyl 6-oxo-8-chloro caprylate, is perfectly solved, and the method is suitable for industrial production. The reaction has the advantages of low cost, easy operation, safe reducing agent and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a method for synthesizing ethyl 6-hydroxy-8-chlorooctanoate, ethyl 6,8-dichlorooctanoate and lipoic acid. Background technique [0002] Lipoic acid is a coenzyme that plays an important role in the tricarboxylic acid cycle of organisms. Lipoic acid has significant antioxidant capacity. In the field of medicine, lipoic acid is widely used in the prevention and treatment of diabetes and its related complications; in the field of health care products, lipoic acid is mainly used to remove free radicals in the body and prevent lipid peroxidation. Protect cells from oxidative damage and achieve the purpose of preventing and assisting the treatment of diseases. [0003] At present, the main method for preparing lipoic acid in the industry at home and abroad is to carry out thiolation reaction between ethyl 6,8-dichlorooctanoate and sodium disulfide, followed by alkaline hydr...

Claims

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Application Information

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IPC IPC(8): C07C67/31C07C69/716C07C67/307C07D339/04
CPCC07C67/31C07C67/307C07D339/04C07C69/716Y02P20/584
Inventor 黄雄志陈建华魏高宁何剑洋刘欣王淞伊静马瑞达
Owner XIAMEN KINGDOMWAY VI TAMIN INC
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