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Method for synthesizing n-decanal ester

The technology of a decaaldehyde ester and a synthetic method is applied in the directions of chemical instruments and methods, preparation of carboxylic acid esters, preparation of organic compounds, etc., and can solve problems such as new routes and methods for synthesis without reports, high price, and no sales, etc., Achieve the effect of good industrialization prospects, simple industrialization operation, and little technical difficulty

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

[0012] The route construction of this method is very good, but it is not suitable for domestic production: the raw material 4-chlorotigrate ethyl ester and the raw material 2-methyl-4,4-diacetoxy-2-butenal are not domestically produced , and there is no sale in the market; the synthesis is very difficult and expensive. At present, there are no new routes and methods for its synthesis reported in China.

Method used

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  • Method for synthesizing n-decanal ester
  • Method for synthesizing n-decanal ester
  • Method for synthesizing n-decanal ester

Examples

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preparation example Construction

[0035] A kind of synthetic method of ten carbon aldehyde ester, comprises the following steps:

[0036] 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 Catalyst reacts 10-15 hour under the p-toluenesulfonic acid effect, adds alkali after reaction and carries out hydrolysis, obtains the acetal product as shown in structural formula (2),

[0037]

[0038] 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;

[0039] 2) The acetal product with the structural formula obtained in the previous step as shown in (2) and the compound vinyl ether with the structural formula as shown in (3) are mixed in an organic solvent according to a molar ratio of 1: 0.8-1.2, at room temperature, a catalyst (ZnBr 2 or FeCl 3 or ZnCl 2 ...

Embodiment 1

[0053] The preparation of the compound shown in structural formula as (9)

[0054]

[0055] 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:

[0056]

Embodiment 2

[0058] The preparation of the compound shown in structural formula as (10)

[0059]

[0060] 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 8 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 the reaction product of 8.5 grams, GC content 98%, and reaction equation is shown as follows:

[0061]

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Abstract

The invention discloses a method for synthesizing n-decanal ester, comprising the following steps of: 1) carrying out acetalation on E-4-acetoxyl group-2-methyl-2-butene-1-aldehyde and trimethyl orthoformate or triethyl orhtoformate, then adding alkali to hydrolyze; 2) reacting a product obtained by the step 1) with vinyl ether; 3) hydrolyzing the product obtained by the step 2); 4) carrying out an Arbuzov reaction on triethyl phosphate and 2-chloropropionic acid ethyl ester in a mole ratio of 1: (1-1.6); 5) in the presence of sodium ethoxide, carrying out a wittig-Horner reaction on a compound obtained by the step 3) and the compound obtained by the step 4), and carrying out an elimination reaction at the temperature of 35-45 DEG C; and 6) oxidizing alcoholic hydroxyl in the compound obtained by the step 5) with TEMPO, thus the n-decanal ester product is obtained after the reaction is completed. All the raw materials adopted in the line of the invention are localized, the raw materials are available, technical difficulty is low, industrialized operation is simple, and industrialization prospect is good.

Description

technical field [0001] The invention relates to a method for synthesizing decaaldehyde esters. Background technique [0002] Decalaldehyde ester is a key intermediate for the synthesis of β-apo-8′-carotene acid ethyl ester, and its structure is as follows: [0003] [0004] Literature U. Schwieter, H Gutmann, H. Lindlar, R. Marbet, N. Rigassi, R. S.F.Schaeren, O.Isler.Helv.Chim.Acta 49, 369-390 (1966). Reported a synthetic method about it is specifically as follows: [0005] [0006] The starting material of this route is hexacarbon alcohol, which is expensive and difficult to synthesize. In the second step, catalytic hydrogenation is used. Due to the active nature of the raw material itself, many by-products are often produced. The final step is oxidation with manganese dioxide. The yield of alcohol into aldehyde is low, and a large amount of waste manganese dioxide is not easy to handle. It is meaningless for the industrialization of the whole route. US 4543417 is...

Claims

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Application Information

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IPC IPC(8): C07C69/73C07C67/313
Inventor 吴世林邸维龙
Owner 安徽智新生化有限公司
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