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Synthetic method for vitamin A intermediate C14 aldehyde

A synthetic method and intermediate technology, which is applied in the field of synthesis of vitamin A intermediates, can solve the problems of difficult product purification and low yield of synthetic methods, and achieve the effects of high yield and purity, simple route, and avoid deterioration

Inactive Publication Date: 2016-01-20
SHANGYU NHU BIOCHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Aiming at the above-mentioned technical problems of the prior art, the present invention provides a synthesis method of vitamin A intermediate C14 aldehyde, which solves the problems of low yield and difficult product purification in the existing synthesis method of C14 aldehyde

Method used

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  • Synthetic method for vitamin A intermediate C14 aldehyde
  • Synthetic method for vitamin A intermediate C14 aldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0031] 1. Preparation of Chloroisobutenyl Methyl Ether Grignard Reagent

[0032] Put 36.5 grams (1.1mol) of magnesium powder in a four-necked flask, add 300ml of tetrahydrofuran, stir vigorously, the temperature rises to 66°C, and add 1 particle of iodine activated magnesium powder, and weigh 132.5 grams (1.1mol) of chlorinated Dissolve isobutenyl methyl ether in 300ml of tetrahydrofuran, slowly drop it into the flask, observe the boiling of tetrahydrofuran, and see that the initiation is successful when a large amount of foam is seen in the flask, then lower the temperature of the water bath to 40°C to cool down the reaction system, and keep the flask The internal reaction was carried out in a slightly boiling state. After the chloroisobutenyl methyl ether was dripped, the temperature was raised to 50° C. and the temperature was continued for 2.0 hours.

[0033] 2. Preparation of C14 aldehyde

[0034] Cool the prepared chloroisobutenyl methyl ether Grignard reagent to -15°C,...

Embodiment 2

[0036] In this embodiment, the acid used is hydrochloric acid, the reaction solvent is methyl tetrahydrofuran, the condensation temperature is from -20°C to 50°C, and the condensation holding time is 1.0-10.0 hours. All the other are identical with embodiment 1.

Embodiment 3

[0038] In this embodiment, the acid used is acetic acid, the reaction solvent is diethyl ether, the condensation temperature is from -20°C to 50°C, and the condensation holding time is 1.0-10.0 hours. All the other are identical with embodiment 1.

[0039] As can be seen from the above examples, a method for synthesizing a vitamin A intermediate C14 aldehyde of the present invention has a simple route, does not need to pass through a β-ionone intermediate, and is directly condensed from cyclic citral, and the yield and purity of the product are high; The product is obtained in an acidic system, which avoids the deterioration of the product in a high temperature and strong alkali environment; the condensate of the chloroisobutenyl methyl ether Grignard reagent is hydrolyzed into olefins and alkene ethers, and the hydrolysis is carried out to obtain aldehydes in one step.

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Abstract

The invention relates to a synthetic method for vitamin A intermediate C14 aldehyde. The synthetic method includes the following steps that 1, cyclocitral is used as a raw material and condensed with a chloro-isocrotyl methyl ether Grignard reagent to prepare a C14 alkenyl ether hydroxyl product; 2, the hydroxy group is hydrolyzed into olefin and alkenyl ether at the same time under acid catalysis to obtain C14 aldehyde. The path of the synthetic method is concise, a beta-ionone intermediate is unnecessary, C14 aldehyde is obtained by directly condensing the cyclocitral, and the yield and the purity of C14 aldehyde are high. The product is obtained in an acid system and prevented from deteriorating in a high-temperature strong base environment; the condensation compound of the chloro-isocrotyl methyl ether Grignard reagent is hydrolyzed into olefin and alkenyl ether to obtain aldehyde through hydrolysis in one step.

Description

technical field [0001] The present invention relates to the synthesis of vitamin A intermediate, in particular to the synthesis method of vitamin A intermediate C14 aldehyde. Background technique [0002] One of the main methods of synthesizing C14 aldehyde is to use β-ionone as raw material to prepare C14 aldehyde through Darzens condensation reaction. This method is also the route currently used in industrial production. The reaction formula is as follows: [0003] [0004] There are following deficiencies in this method: [0005] (1) The yield is low, and the reaction needs to be carried out under relatively harsh conditions; [0006] (2) Many side reactions make product purification difficult. [0007] Therefore, some researchers have proposed the methyl sulfide method, and the reaction formula is as follows: [0008] [0009] However, the methyl sulfide method uses expensive methyl iodide and the dangerous strong base DMSO sodium salt in the preparation, and t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/225C07C45/42
CPCC07C45/42C07F3/02C07C47/225
Inventor 曾庆宇钟为水吕国锋王平珍杨洁吴嘉圣吴美丽
Owner SHANGYU NHU BIOCHEM IND
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