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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 preparation process of the C14 or C15 intermediate used is cumbersome, and the post-treatment Complexity, poor operation safety, harsh reaction conditions, high cost, poor atom economy, large amount of waste water, not environmentally friendly, and low yield and purity, so the development and optimization of a low-cost green industrial process for vitamin A ester intermediate C15, for vitamin A The industrial production of A esters (vitamin A acetate and vitamin A palmitate, etc.) is of great significance

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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