Preparation method of vitamin A intermediate tetradecanal

A technology of tetradecaldehyde and intermediate, which is applied in the field of preparation of vitamin A intermediate tetradecaldehyde, can solve the problems of low yield of vitamin A intermediate tetradecaldehyde and the like

Pending Publication Date: 2022-04-29
XIAMEN KINGDOMWAY VI TAMIN INC +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to overcome the defect that the yield is low when adopting the existing method to prepare vitamin A intermediate tetradecaldehyde, and to provide a kind of preparation of vitamin A intermediate tetradecaldehyde that can obtain high yield method

Method used

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  • Preparation method of vitamin A intermediate tetradecanal
  • Preparation method of vitamin A intermediate tetradecanal

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preparation example Construction

[0030] The preparation method of the vitamin A intermediate tetradecaldehyde provided by the invention comprises the following steps: S1, carrying out Darzens condensation reaction of β-ionone, sodium methylate and methyl chloroacetate to obtain epoxy carboxylate methanol solution; S2, making the Said methanol solution of epoxy carboxylate is subjected to saponification reaction with water to obtain a solution containing sodium epoxy carboxylate; S3, adding non-polar solvent I to the solution containing sodium epoxy carboxylate and then separating the solid and liquid to obtain filter cake and filtrate , adding water to the filtrate and stirring, then standing and stratifying to obtain an upper oil phase and a lower water phase; the upper oil phase is desolvated to obtain unreacted β-ionone, which is directly applied to the Darzens condensation reaction; The lower aqueous phase and the filter cake are decarboxylated together with an aqueous alkali solution, and after the decarb...

Embodiment 1

[0045] S1, using 100g β-ionone, 70.23g sodium methoxide, and 84.65g methyl chloroacetate as raw materials, prepared an epoxy carboxylate methanol solution with an epoxy carboxylate content of 36.8% through Darzens reaction for 8 hours at -30°C 375mL;

[0046] S2. Add 14 mL of water to the methanol solution of epoxy carboxylate, stir at -5°C for 1.5 h to carry out saponification reaction to obtain a solution containing sodium epoxy carboxylate;

[0047] S3, the saponification reaction is completed, add 40mL sherwood oil to the described epoxy carboxylate-containing sodium solution, filter, add 40mL water to the obtained filtrate and stir and leave to stand for stratification to obtain the upper oil phase and the lower water phase; the upper layer The oil phase was concentrated under reduced pressure to remove the solvent to obtain 2.77g oily matter, wherein the content of β-ionone was 97.3%; the lower water phase was added to the filter cake, and the lower filter cake layer was...

Embodiment 2

[0049] S1. Using 100g of β-ionone, 70.23g of sodium methoxide, and 84.65g of methyl chloroacetate as raw materials, 373mL of epoxy carboxylate methanol solution with an epoxy carboxylate content of 37% was prepared by Darzens reaction at 15°C for 3h ;

[0050] S2. Add 18.7mL of water to the methanol solution of epoxy carboxylate, stir at -5°C for 1.5h to carry out saponification reaction to obtain a solution containing sodium epoxy carboxylate;

[0051] S3, the saponification reaction is completed, add 80mL n-pentane to the sodium epoxy carboxylate solution, filter, add 80mL water to the resulting filtrate, stir and leave to separate to separate, to obtain the upper oil phase and the lower water phase; The upper oil phase was concentrated under reduced pressure to remove the solvent to obtain 2.72g oily matter, wherein the content of β-ionone was 97.5%; the lower layer water phase was added to the filter cake, and the lower filter cake layer was stirred and 104g of 40.0% sodiu...

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Abstract

The invention belongs to the field of organic synthesis, and relates to a preparation method of a vitamin A intermediate tetradecanal, which comprises the following steps: carrying out Darzens condensation reaction on beta-ionone, sodium methoxide and methyl chloroacetate, carrying out saponification reaction on the obtained epoxy carboxylic ester methanol solution and water, adding a non-polar solvent I into the obtained epoxy carboxylic acid sodium solution, and carrying out solid-liquid separation, adding water into the filtrate, stirring, and standing for layering to obtain an upper oil phase and a lower water phase; removing the solvent from the upper oil phase to obtain unreacted beta-ionone, and directly applying the unreacted beta-ionone to the Darzens condensation reaction; a lower-layer water phase and the filter cake are subjected to decarboxylation together with an aqueous alkali solution, lithium salt is added for an isomerization reaction after decarboxylation is completed, water and a non-polar solvent II are added into an obtained isomerization reaction product, the mixture is stirred and then stands for layering, an obtained supernatant liquid is sequentially subjected to acid pickling and water washing, the solvent is removed, and then reduced pressure distillation is conducted to obtain tetradecanal. The method provided by the invention can improve the yield of tetradecanal.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of vitamin A intermediate tetradecaldehyde. Background technique [0002] The full name of tetradecaldehyde is 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, which is an important intermediate for the preparation of vitamin A by the Roche process , which has the structure shown in formula (1): [0003] [0004] At present, the main preparation technology of tetradecaldehyde is to carry out Darzens condensation reaction to obtain epoxy carboxylate by β-ionone (having the structure shown in formula (2)) and methyl chloroacetate, and described epoxy carboxylate is again Prepared by saponification decarboxylation. [0005] [0006] CN101268044A discloses a kind of technology that takes solid sodium methylate as base and prepares myristal in the presence of dipolar aprotic compound; CN103408410A discloses a kind of device for prepari...

Claims

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Application Information

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IPC IPC(8): C07C403/14
CPCC07C403/14
Inventor 马瑞达朱少军戴剑坤林兴
Owner XIAMEN KINGDOMWAY VI TAMIN INC
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