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Method for synthesizing decyl acetal aldehyde

A technology for the synthesis of ten-carbon acetal and its synthesis method, which is applied in the field of synthesis of ten-carbon acetal, can solve the problems of numerous steps, high cost, and low yield, and achieve simple industrial operation, good industrialization prospects, and technical difficulty little effect

Active Publication Date: 2012-03-28
安徽智新生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This route has many steps, is difficult, and needs to undergo catalytic hydrogenation, the yield is low, and the cost is high; and there is no new synthesis method about it reported in China

Method used

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  • Method for synthesizing decyl acetal aldehyde
  • Method for synthesizing decyl acetal aldehyde
  • Method for synthesizing decyl acetal aldehyde

Examples

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Effect test

preparation example Construction

[0025] A kind of synthetic method of ten carbon acetals, comprises the following steps:

[0026] 1) Compound (E-4-acetoxy-2-methyl-2-butene-1-aldehyde) represented by structural formula (1) and trimethyl orthoformate or triethyl orthoformate at room temperature, acidic Carry out acetalization reaction under the effect of catalyzer p-toluenesulfonic acid, add alkali to carry out hydrolysis again after reaction finishes, obtain the acetal product as shown in structural formula (2),

[0027]

[0028] Among them, R 1 It is methyl or ethyl, and the molar ratio of the compound shown in structural formula (1), trimethyl orthoformate or triethyl orthoformate, and base is 1: 0.8-1.5: 0.6-1.2;

[0029] 2) the acetal product obtained in the previous step and the vinyl ether compound shown in (3) according to the molar ratio of 1: 0.8-1.2 at room temperature, catalyst (zinc chloride, zinc bromide, trichloride A kind of in iron) reacts under the effect, obtains the product of structur...

Embodiment 1

[0041] The preparation of the compound shown in structural formula as (8)

[0042]

[0043] Get 10 grams of the compound shown in structural formula (1), add catalytic amount of p-toluenesulfonic acid, add 10 grams of trimethyl orthoformate, react at room temperature for 10 hours, add 2 grams of hydrogen after the reaction finishes Sodium oxide, stirred and reacted for 6 hours, then added 200 milliliters of water, extracted three times with dichloromethane, 50 milliliters each time, combined the organic phases, backwashed the organic layer with 5% saline, 50 milliliters each time, dried with potassium carbonate, Filter, evaporate the solvent to dryness, and distill under reduced pressure to obtain 9 grams of the reaction product, the GC content is 98%, and the reaction equation is shown as follows:

[0044]

[0045]

Embodiment 2

[0047] The preparation of the compound shown in structural formula as (9)

[0048]

[0049] Get 10 grams of the compound shown in structural formula (1), add catalytic amount of p-toluenesulfonic acid, add 11 grams of triethyl orthoformate, react at room temperature for 15 hours, add 2 grams of hydrogen after the reaction finishes Sodium oxide, stirred and reacted for 7 hours, then added 200 milliliters of water, extracted three times with dichloromethane, 50 milliliters each, combined the organic phases, backwashed the organic layer with 5% saline, 50 milliliters each, dried with potassium carbonate, Filter, evaporate the solvent to dryness, and distill under reduced pressure to obtain 10 grams of the reaction product, the GC content is 97%, and the reaction equation is shown as follows:

[0050]

[0051]

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Abstract

The invention discloses a method for synthesizing decyl acetal aldehyde. The method comprises the following steps of: 1) performing acetalation reaction of E-4-acetoxy-2-methyl-2-butene-1-aldehyde and trimethoxymethane or triethyl orthoformate, and adding alkali for hydrolyzing; 2) reacting the obtained product with a vinyl ether compound to obtain a product, and reacting the product with an allyl ether compound; 3) adding the product obtained in the step 2) into alkaline solution, and reacting at the temperature of between 30 and 50 DEG C for 1 to 5 hours; and 4) oxidizing alcoholic hydroxyl of the compound obtained in the steps 3) to obtain a final decyl acetal aldehyde product. In the method, all raw materials related in a route are subjected to domestication and are low in cost, and the method is small in technical difficulty and easy to operate industrially and has a bright industrial prospect.

Description

technical field [0001] The invention relates to a method for synthesizing ten-carbon acetal. Background technique [0002] Ten-carbon acetal is a key intermediate for the synthesis of β-apo-8′-carotene aldehyde, and its structure is as follows: [0003] [0004] Helv.Chim.Acta49, 369-390 (1966), the operational route of the decacarbon acetal of report is starting raw material with hexacene alkyne alcohol, specifically as follows: [0005] [0006] This route has many steps, is difficult, and needs to undergo catalytic hydrogenation, with low yield and high cost; and there is no new synthesis method about it reported in China. Contents of the invention [0007] The purpose of this invention is to provide a kind of synthetic method of ten carbon acetals. [0008] The technical scheme that the present invention takes is: [0009] A kind of synthetic method of ten carbon acetals, comprises the following steps: [0010] 1) The compound represented by structural formul...

Claims

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Application Information

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IPC IPC(8): C07C47/277C07C45/34
Inventor 邸维龙吴世林
Owner 安徽智新生化有限公司
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