Preparation method of vitamin A ester intermediate C15 and vitamin A ester

A technology for vitamins and intermediates, which is applied in the field of preparation of vitamin A ester intermediate C15 and vitamin A ester, can solve the problems of complicated post-processing, low purity of vitamin A palmitate, unenvironmental protection and the like

Active Publication Date: 2020-08-04
XINFA PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0025]Vitamin A palmitate is prepared by transesterification of vitamin A acetate, esterification of vitamin A alcohol and palmitoyl chloride or transesterification of vitamin A alcohol and palmitate , but the existing methods are unfavorable for controlling the impurity content of vitamin A alcohol, palmitate and vitamin A acetate, and the purity of the obtained vitamin A palmitate is relatively low
[0026] In summary, although the C15+C5 route of vitamin A acetate has certain industrial value, the prep

Method used

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  • Preparation method of vitamin A ester intermediate C15 and vitamin A ester
  • Preparation method of vitamin A ester intermediate C15 and vitamin A ester
  • Preparation method of vitamin A ester intermediate C15 and vitamin A ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0122] Example 1: 2,6,6-trimethyl-2-chloromethylcyclohexene (Ⅲ 1 ) preparation

[0123] Add 500 g of 1,2-dichloroethane, 154.0 g (1.0 mol) of 3,7-di Methyl-3-hydroxy-1,6-octadiene, 131.0 g (1.1 moles) of thionyl chloride, kept between 40°C and 45°C, stirred for 3 hours, cooled to 10-15°C to obtain chlorinated The reaction liquid was transferred to a constant pressure dropping funnel and set aside. In another 1000 ml four-necked flask equipped with stirring, thermometer, reflux condenser and constant pressure dropping funnel, add 100 g of 1,2-dichloroethane, 5.0 g of 98% concentrated sulfuric acid, and keep it at 70°C to 75°C. Between ℃, add the obtained chlorination reaction liquid dropwise, and the dropwise addition is completed in 2 hours. After that, stir and react at 70℃~75℃ for 3 hours, cool to 10-15℃, add 100 grams of water, stand to separate layers, and distill the organic phase After recovering the solvent, 171.0 grams of colorless liquid 2,6,6-trimethyl-2-chloromet...

Embodiment 2

[0124] Example 2: 2,6,6-trimethyl-2-chloromethylcyclohexene (Ⅲ 1 ) preparation

[0125] Under nitrogen protection, add 500 g of dichloromethane, 154.0 g (1.0 mole) of 3,7-dimethyl Base-3-hydroxyl-1,6-octadiene, 135.6 g (1.3 moles) of 35% hydrochloric acid aqueous solution, kept between 30°C and 35°C, stirred and reacted for 2 hours, cooled to 10-15°C, and separated into layers to obtain The organic phase is the chlorination reaction liquid, which is transferred to a constant-pressure dropping funnel for later use. In another 1000 ml four-necked flask equipped with stirring, thermometer, reflux condenser and constant pressure dropping funnel, add 100 g of dichloromethane, 5.0 g of 98% concentrated sulfuric acid, keep between 35°C and 40°C, drop Add the obtained chlorinated reaction liquid, drop it in 2 hours, after that, stir and react at 35°C to 40°C for 4 hours, cool to 10-15°C, add 100 grams of water, stand to separate layers, and distill the organic phase to recover the s...

Embodiment 3

[0126] Example 3: 2,6,6-trimethyl-2-bromomethylcyclohexene (Ⅲ 2 ) preparation

[0127] Under nitrogen protection, add 500 g of dichloromethane, 154.0 g (1.0 mole) of 3,7-dimethyl Base-3-hydroxy-1,6-octadiene, 220.0 g (1.1 mol) 40% hydrobromic acid aqueous solution, kept between 30°C and 35°C, stirred for 2 hours, cooled to 10-15°C, separated , the organic phase was obtained as a bromination reaction liquid, which was transferred to a constant pressure dropping funnel for subsequent use. In another 1000 ml four-necked flask equipped with stirring, thermometer, reflux condenser and constant pressure dropping funnel, add 100 g of dichloromethane, 5.0 g of 98% concentrated sulfuric acid, keep between 35°C and 40°C, drop Add the obtained bromination reaction liquid, and drop it in 2 hours. After that, stir and react at 35°C to 40°C for 3 hours, cool to 10-15°C, add 100 grams of water, let stand to separate layers, and distill the organic phase to recover the solvent to obtain 19...

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Abstract

The invention provides a preparation method of a vitamin A ester intermediate C15 and vitamin A ester. The method comprises the following steps: carrying out a halogenation reaction and a cyclizationreaction on 3, 7-dimethyl-3-hydroxy-1, 6-octadiene as an initial raw material, carrying out a substitution reaction on the obtained product and triphenylphosphine or triester phosphite to prepare a corresponding Wittig reagent, carrying out a Wittig reaction on the Wittig reagent and 2-methyl-4-acetoxy-2-butenal, performing acidifying, hydrolyzing and acidifying the obtained product, and carryingout a substitution reaction on the hydrolyzed and acidified product and triphenylphosphine or triester phosphite to prepare C15. The vitamin A ester can be prepared by carrying out a Wittig reaction on the obtained C15 and 2-methyl-4-R3 substituent carbonyloxy-2-butenal. The method has the advantages of single reaction type, easy operation and realization of reaction conditions, safe and environment-friendly operation, simple post-treatment and low cost; and the reaction activity is strong, the reaction selectivity is high, the atom economy is high, and the target product yield and purity arehigh.

Description

technical field [0001] The invention relates to a preparation method of vitamin A ester intermediate C15 and vitamin A ester, belonging to the technical field of fine chemical industry and medicine. Background technique [0002] Vitamin A and its derivatives are an important class of pharmaceuticals and feed additives. Commonly used vitamin A derivatives are vitamin A esters, especially vitamin A acetate and vitamin A palmitate. [0003] Vitamin A acetate, also known as retinyl acetate, vitamin A acetate, CAS number 127-47-9, is a light yellow solid powder with good fluidity. Vitamin A acetate has a variety of important physiological functions, and is an essential nutrient for vision system, growth, epithelial tissue and bone development, sperm production and fetal growth and development. Vitamin A acetate plays an important role in many life activities, such as vision generation, growth, development, differentiation, metabolism and morphogenesis, and can be used to treat n...

Claims

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Application Information

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IPC IPC(8): C07F9/54C07F9/40C07C403/12C07C21/19C07C17/16C07C22/02C07C17/358C07C403/04
CPCC07F9/5442C07F9/4075C07F9/4018C07C403/12C07C17/16C07C17/358C07C403/04C07C2601/16C07C21/19C07C22/02
Inventor 戚聿新周立山腾玉奇江枭南
Owner XINFA PHARMA
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