Method for producing improved vitamin A acetic ester

A technology of acetate and vitamin, which is applied in the field of preparation of vitamin A acetate, can solve the problems of high difficulty in industrial operation, high energy consumption, unfavorable large-scale production, etc., and achieve the reduction of energy consumption and the difficulty of production operation, high Yield, the effect that is conducive to industrialized production

Active Publication Date: 2008-07-16
安徽智新生化有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The solvent used in this method is polar solvent DMSO, DMF and non-polar solvent toluene, n-hexane, etc.; the reaction temperature can be -70 ° C ~ 70 ° C, but to achieve a higher yield

Method used

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  • Method for producing improved vitamin A acetic ester
  • Method for producing improved vitamin A acetic ester

Examples

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example 1

[0022] Diethyl 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonate (10g, content 95.5% , 27.5mmol) was dissolved in 80ml of toluene, then 1.5g of sodium methoxide and 20ml of pyridine were added, the temperature was adjusted and maintained at 20°C, and stirred under nitrogen protection for 5 minutes, the 4-acetoxy-2-methyl- 2-butene-1 aldehyde (5g, content is 99%, 35mmol) is added dropwise in the toluene solution of 20ml with the time of 20 minutes, continues to react for half an hour; Add water 150ml, stir layering, separate and take organic layer, Dry and evaporate to dryness under reduced pressure to obtain 11.5g of yellow solid; add 100ml of methanol, cool to -10°C, stand for 3 hours, crystallize, filter to obtain 10.5g of light yellow solid, according to the appendix of "Chinese Pharmacopoeia 2005 Edition" (Part II) The first method in VIIJ vitamin A determination method (Appendix 45-47 pages), the detection yield is 91.5%.

example 2

[0024] Diethyl 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadienylphosphonate (10g, content 95.5% , 27.5mmol) was dissolved in 80ml of toluene, then 2g of sodium ethoxide and 25ml of 3-picoline were added, the temperature was maintained at 30°C, and stirred under nitrogen protection for 5 minutes, the 4-acetoxy-2-methyl- 2-butene-1 aldehyde (5g, content is 99%, 35mmol) is added dropwise in 20ml of toluene solution with the time of 20 minutes, continue to react for half an hour after dropping, add water 150ml, stir layering, separate The organic layer was taken, dried, and evaporated to dryness under reduced pressure to obtain 11.5 g of a yellow solid, then 100 ml of methanol was added, cooled to -10° C., left for 3 hours, crystallized, and filtered to obtain 9.5 g of a light yellow solid. According to "Chinese Pharmacopoeia 2005 Edition" ( Part 2) The first method in the vitamin A determination method of Appendix VIIJ (appendix 45-47 pages), the detection yield is 8...

example 3

[0026] Dipropyl 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,4-pentadienylphosphonate (10g, content 95.5% , 25.2mmol) was dissolved in 85ml of toluene, then 1.8g of sodium ethoxide and 20ml of 2,5-lutidine were added, the temperature was maintained at 25°C, and the nitrogen protection was stirred for 10 minutes, and the 4-acetoxy-2 -Methyl-2-butene-1 aldehyde (5g, content is 99%, 35mmol) is added dropwise in the toluene solution of 10ml with the time of 15 minutes, continue to react for 20 minutes after dropping, add water 150ml, stir to divide layer, the organic layer was separated, dried, evaporated to dryness under reduced pressure to obtain 11g of yellow solid, then added 100ml of methanol, cooled to -10°C, left for 3 hours, crystallized, filtered to obtain 10g of light yellow solid, according to "Chinese Pharmacopoeia 2005 Edition" (Part Two) The first method in the vitamin A assay method of Appendix VIIJ (appendix 45-47 pages), the detection yield is 88%.

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Abstract

The invention provides an improved preparation method for vitamin A acetate, which adopts a route of C15+C5 with Wittig reaction as characteristics, namely, using a carbon 15 phosphonic acid dialkyl ester and a C 5-aldehyde to react under the function of alkali to generate the vitamin A acetate. The invention is characterized in that a mixture of toluene and pyridine (or the methyl substitutes of pyridine) is used as a reaction solvent to enable the reaction to be carried on in an environment close to a room temperature and to reach the yield that can be achieved only under extremely low temperature, which greatly reduces the energy consumption and the difficulties of production operation and is beneficial to industrial production.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a preparation method of conjugated polyene unsaturated carbon frame compounds, in particular to a preparation method of vitamin A acetate. Background technique [0002] Vitamin A and its derivatives are important medicines for the treatment of night blindness, dry eyes, corneal softening, and dry skin. an important feed additive. Commonly used vitamin A derivatives are its alkyl esters, such as acetate, propionate, palmitate, etc., and its structure is shown in the following formula (R 1 for alkyl): [0003] [0004] Among the many derivatives of vitamin A, acetate is the most commonly used. At present, the technical route of synthesizing vitamin A acetate mainly contains following 3 kinds: 1, the C that is characterized by Grignard reaction 14 +C 6 Route: Using β-ionone as raw material, it is completed through six steps of Darzens reaction, Grignard reaction, hydrogenati...

Claims

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Application Information

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IPC IPC(8): C07C403/12
Inventor 吴世林邸维龙
Owner 安徽智新生化有限公司
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