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

The technology of acetate and vitamin is applied in the field of preparation of vitamin A acetate intermediate C15 and vitamin A acetate, and can solve the problems of unenvironmental protection, complicated post-treatment, large amount of waste water and the like

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

AI Technical Summary

Problems solved by technology

[0027] 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, the post-treatment is complicated, the operation safety is poor, the reaction conditions are harsh, the cost is high, and the atomic Poor economy, large amount of waste water, not environmentally friendly, low yield and purity, so the development and optimization of vitamin A acetate intermediates is of great significance for the industrial production of vitamin A acetate

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] Embodiment 1: Formula III 1 Compound preparation

[0107] Formula III 1 The structural formula of the compound is as follows:

[0108]

[0109] Under nitrogen protection, add 250 grams of acetonitrile, 41.5 grams (0.2 moles) of 1-bromo-2-methyl-4-acetoxy-2-butyl alkene (II 1 ), 52.5 grams (0.2 moles) of triphenylphosphine, stirred and reacted at 60-65°C for 4 hours, cooled to 10-15°C, filtered, and obtained 89.2 grams of formula III after drying the filter cake 1 Compound, the filtrate was calibrated with a liquid-phase external standard method to have a triphenylphosphine content of 2.63 grams, which can be directly applied to the next batch of reactions. The calculated yield based on the actual conversion of triphenylphosphine was 99.9%, and the liquid-phase purity was 99.7%.

Embodiment 2

[0110] Embodiment 2: Formula III 2 Compound preparation

[0111] Formula III 2 The structural formula of the compound is as follows:

[0112]

[0113] Under nitrogen protection, add 250 grams of acetonitrile, 34.1 grams (0.21 moles) of 1-chloro-2-methyl-4-acetoxy-2-butyl alkene (II 2 ), 52.5 grams (0.2 moles) of triphenylphosphine, stirred and reacted at 70-75°C for 4 hours, cooled to 10-15°C, filtered, and obtained 77.8 grams of formula III after drying the filter cake 2 Compound, the filtrate was calibrated with a liquid-phase external standard method to have a triphenylphosphine content of 4.46 grams, which can be directly applied to the next batch of reactions. The calculated yield based on the actual conversion of triphenylphosphine was 99.9%, and the liquid-phase purity was 99.5%.

Embodiment 3

[0114] Embodiment 3: Formula III 3 Preparation of compound (diethyl 2-methyl-4-acetoxy-2-butenylphosphonate)

[0115] Formula III 3 The structural formula of the compound is as follows:

[0116]

[0117] Under nitrogen protection, add 41.5 grams (0.2 moles) of 1-bromo-2-methyl-4-acetoxy-2-butene (II 1 ), 41.6 grams (0.25 moles) of triethyl phosphite, stirred and reacted at 105-110°C for 4 hours (using ethanol to recover the generated by-product bromoethane), cooled to 70-75°C, replaced with a vacuum distillation device, and recovered After excessive triethyl phosphite, further underpressure distillation (110-120 ℃ / 1-2mmHg) obtains 49.6 grams of 2-methyl-4-acetoxy-2-butenyl phosphonic acid diethyl ester (Ⅲ 3 ), the yield is 93.9%, and the gas phase purity is 99.2%.

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Abstract

The invention provides a preparation method of a vitamin A acetate intermediate C15 and vitamin A acetate. The method comprises the following steps: taking 1-halogenated-2-methyl-4-acetoxy-2-butene asa raw material, preparing a corresponding Wittig reagent through a substitution reaction with triphenylphosphine or triester phosphite, then carrying out a Wittig reaction with beta-cyclocitral, hydrolyzing an ester group under an alkaline condition, acidifying to obtain a corresponding halide, and carrying out a substitution reaction with triphenylphosphine or triester phosphite again to prepareC15. The vitamin A acetate can be prepared by carrying out a Wittig reaction on the obtained C15 and 2-methyl-4-acetoxy-2-butenal under an alkaline condition. The method has the advantages of singlereaction 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 are high.

Description

technical field [0001] The invention relates to a vitamin A acetate intermediate C15 and a preparation method of vitamin A acetate, belonging to the technical fields of fine chemical industry and medicine. Background technique [0002] Vitamin A and its derivatives are an important class of pharmaceuticals and feed additives, and the most commonly used vitamin A derivative is vitamin A acetate. Vitamin A acetate, also known as vitamin A acetate, retinyl acetate, vitamin A acetate, CAS number 127-47-9, is a light yellow solid powder with good fluidity. The structural formula of vitamin A acetate is as follows: [0003] [0004] vitamin A acetate [0005] 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, de...

Claims

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Application Information

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IPC IPC(8): C07F9/54C07F9/40C07C67/293C07C69/145C07C17/093C07C22/02
CPCC07F9/5442C07F9/4006C07C67/293C07C17/093C07C2601/16C07C69/145C07C22/02
Inventor 戚聿新江枭南腾玉奇刘思尧
Owner XINFA PHARMA
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