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,...

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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