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Purification method of 8-oxo-3, 7-dimethyl-octadiene carboxylic ester compound

A technology of octadienyl carboxylate and purification method, which is applied in the separation/purification of carboxylate, the preparation of organic compounds, the preparation of carboxylate, etc., can solve problems such as being unsuitable for large-scale production, and achieve a simple process Effect

Active Publication Date: 2020-06-12
广州巨元生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obtaining purified 8-oxo-3,7-dimethyl-octadienyl acetate compound requires column chromatography, which is very unsuitable for large-scale production

Method used

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  • Purification method of 8-oxo-3, 7-dimethyl-octadiene carboxylic ester compound
  • Purification method of 8-oxo-3, 7-dimethyl-octadiene carboxylic ester compound
  • Purification method of 8-oxo-3, 7-dimethyl-octadiene carboxylic ester compound

Examples

Experimental program
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Effect test

Embodiment 1

[0038] 45.0g crude 8-oxo-3,7-dimethyl-octadienyl formate compound (content of 8-oxo-3,7-dimethyl-octadienyl formate (cis Formula + trans): 67.5%) is miscible with 50g of methanol, and then added dropwise to 69.0g of 35% sodium bisulfite aqueous solution with a mass percentage of 69.0g, the temperature was kept at 60°C, the dropwise addition was completed in 0.5h, and then reacted for 4h , The reaction of 8-oxo-3,7-dimethyl-octadienyl formate was complete by gas phase detection. Recover methanol by distillation from the reaction mixture, extract the organic phase three times with 120ml dichloromethane, and separate The aqueous layer of sodium sulfonate, in the gained aqueous layer, add the dichloromethane of 100ml, at normal temperature, slowly add dropwise to wherein the mass percentage of 101.7g be 10% hydrochloric acid aqueous solution, the gained reaction mixture is stirred at normal temperature for 1 hours to react. After the reaction was completed, the reaction mixture ...

Embodiment 2

[0040] 40.0g crude 8-oxo-3,7-dimethyl-octadienyl propionate compound (8-oxo-3,7-dimethyl-octadienyl propionate content (cis Formula + trans): 62.5%) is miscible with 50g of methanol, then added dropwise to 49.7g of 35% sodium bisulfite aqueous solution with a mass percentage of 35%, the temperature was kept at 60°C, the dropwise addition was completed in 0.5h, and then reacted for 4h , The reaction of 8-oxo-3,7-dimethyl-octadienyl propionate was completed by gas phase detection. Recover methanol by distillation from the reaction mixture, extract the organic phase three times with 120ml dichloromethane, and separate the The aqueous layer of sodium sulfonate, in the gained aqueous layer, add the dichloromethane of 100ml, at normal temperature, to wherein dropwise add 33.2g of the mass percent of 20% sodium hydroxide aqueous solution, the gained reaction mixture is stirred at normal temperature 1 hour for reaction. After the reaction was complete, the pH of the aqueous layer wa...

Embodiment 3

[0042] The crude 8-oxo-3,7-dimethyl-octadienyl acetate compound of 70.0g (the content of 8-oxo-3,7-dimethyl-octadienyl acetate (cis Formula + trans): 65.0%) is miscible with 80g of methanol, and then added dropwise to 97.0g of 35% aqueous sodium bisulfite solution with a mass percentage of 97.0g, the temperature was kept at 60°C, the dropwise addition was completed in 0.5h, and then reacted for 4h , gas phase detection of 8-oxo-3,7-dimethyl-octadienyl acetate was completely reacted, and methanol was recovered by distillation from the reaction mixture. Use 150ml dichloromethane to extract the organic phase three times, separate the aqueous layer containing α-hydroxyl [8-acetoxyl-2,6-dimethyl-2,6-octadienyl] sodium sulfonate, and add to the obtained 150ml of dichloromethane was added to the water layer, and 64.9g of 20% by mass sodium hydroxide aqueous solution was added dropwise thereto at room temperature, and the resulting reaction mixture was stirred at room temperature for ...

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Abstract

The invention discloses a purification method of a 8-oxo-3, 7-dimethyl-octadiene carboxylic ester compound. The by-products generated in the reaction process of preparing the 8-oxo-3, 7-dimethyl-octadiene carboxylic ester compound and impurities derived from raw materials can be effectively removed; the process is simple under normal pressure, the purity of the 8-oxo-3, 7-dimethyl-octadiene carboxylic ester compound can be effectively improved, the method is suitable for industrial mass production, and subsequent production of vitamin A and carboxylic esters thereof is facilitated.

Description

technical field [0001] The invention relates to the field of fine organic synthetic chemistry, in particular to a method for purifying 8-oxo-3,7-dimethyl-octadienyl carboxylate compounds. Background technique [0002] 8-oxo-3,7-dimethyl-octadienyl carboxylate compound is an important intermediate in the synthesis of vitamin A and its carboxylates, carotenoids and coenzyme Q. As a method for preparing this 8-oxo-3,7-dimethyl-octadienyl carboxylate compound, the Dutch Duphar company has used 8-acyloxy-2,6-dimethyl-1- Hydroxy-2,6-octadiene compound oxidation method (eg patent, US5196608A), Japan Kuraray company uses 8-acetoxy-2,6-dimethyl-1-hydroxyl-2,6-octadiene compound Oxidation method (for example patent, JPH078827B2), method for oxidation with 6-chloro-3,7-dimethyl-2,7-octadienyl acetate compound (for example patent, EP0234496B2), and by 2,6 -A method for oxidation of dimethyl-2,6-octadiene-8-acetate compound (for example, patent, US4876400A) and the like. [0003] The ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/48C07C67/60C07C69/07C07C69/145C07C69/24
CPCC07C67/48C07C67/60C07C69/07C07C69/145C07C69/24
Inventor 许坤关裕时
Owner 广州巨元生化有限公司
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