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Preparation method of tiglic aldehyde derivative

A derivative, tiglic aldehyde technology, applied in the field of preparation of tiglic aldehyde derivatives, can solve the problems of poor product yield, difficult post-processing, high reaction temperature, etc., so as to save equipment cost and production cost, and reduce equipment cost. Equipment and operators, the effect of simple process

Active Publication Date: 2018-05-08
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the high reaction temperature, the product yield is not good
[0008] Therefore, in view of the existing problems in the preparation of tiglic aldehyde derivatives, such as cumbersome process, low yield, and difficult post-processing, it is urgent to find a new process for preparing tiglic aldehyde derivatives to solve the above-mentioned deficiencies

Method used

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  • Preparation method of tiglic aldehyde derivative
  • Preparation method of tiglic aldehyde derivative
  • Preparation method of tiglic aldehyde derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0039]Synthesis of chlorotiglic aldehyde:

[0040] In a 500mL reactor, put 10.66g (0.1mol) of 2-methyl-4-chloro-2-butene, 210g of isopropanol aqueous solution, 0.11g of formaldehyde and SeO 2 2.1g, stir evenly, then heat up to 50°C, keep stirring under normal pressure for 5 hours, after the reaction is complete, the reaction solution is cooled to room temperature, and after standing to separate layers, the oil phase is at a reflux ratio of 2:1, and the top pressure is Absolute pressure 100Pa, the rectifying column that total number of plates is 80 separates and obtains chloro tiglic aldehyde 86.6g (GC analysis, purity is 98%), and reaction yield is 71.5%.

[0041] The 1H-NMR spectrogram of gained product chloro tiglic aldehyde is as follows figure 1 shown.

Embodiment 2

[0043] Synthesis of bromotiglic aldehyde:

[0044] In a 500mL reactor, put 15.11g (0.1mol) of 2-methyl-4-bromo-2-butene, 210g of isopropanol aqueous solution, 0.11g of formaldehyde and SeO 2 2.1g, stir evenly, then heat up to 55°C, keep stirring under normal pressure for 4 hours, after the reaction is complete, the reaction solution is cooled to room temperature, and after standing to separate layers, the oil phase is at a reflux ratio of 2:1, and the top pressure is Absolute pressure 100Pa, the rectifying column that total number of plates is 80 separates and obtains bromo tiglic aldehyde 130.3g (GC analysis, purity is 98%), and the reaction yield is 78.3%.

[0045] The 1H-NMR spectrogram of the resulting product bromotiglic aldehyde is shown in figure 2 shown. :

Embodiment 3

[0047] Synthesis of γ-phenyl tiglic aldehyde:

[0048] In a 500mL reactor, put 14.82g (0.1mol) of 2-methyl-4-phenyl-2-butene, 210g of isopropanol aqueous solution, 0.11g of formaldehyde and SeO 2 2.1g, stir evenly, then heat up to 60°C, keep stirring under normal pressure for 4 hours, after the reaction is complete, the reaction solution is cooled to room temperature, and after standing to separate layers, the oil phase is at a reflux ratio of 2:1, and the top pressure is The absolute pressure was 100 Pa, and the rectification tower with a total plate number of 80 was separated to obtain 115.6 g of γ-phenyl tiglic aldehyde (GC analysis, purity 98.8%), and the reaction yield was 71.3%.

[0049] The 1H-NMR spectrum of the resulting product γ-phenyl tiglic aldehyde is shown in image 3 .

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Abstract

The invention provides a preparation method of a tiglic aldehyde derivative. The preparation method comprises the following step of carrying out catalytic oxidation on an isoamylene derivative represented as the following formula (I) in the presence of a catalyst to produce the tiglic aldehyde derivative represented as the following formula (II), wherein the catalyst is a non-metal oxide, and theR in the formula (I) or the formula (II) is selected from aliphatic hydrocarbyl, aryl, aralkyl, halogens, ester groups, acyloxy, acylamino or alkoxy. The preparation method of the tiglic aldehyde derivative provided by the invention has the characteristics of few reaction step, simple process, cheap and easily available raw materials and the like.

Description

technical field [0001] The invention relates to the technical field of preparation of tiglic aldehyde derivatives, in particular to a preparation method of tiglic aldehyde derivatives. Background technique [0002] Tiglic aldehyde derivatives, also known as Argyle aldehyde derivatives. In the food industry, tiglic aldehyde derivatives can be used to prepare food flavors such as vanilla, tropical fruits, almonds, and cherries; An important intermediate of aldehyde and vitamin A. Tiglic aldehyde derivatives can also be used in the synthesis of other organic compounds. [0003] Tiglic aldehyde derivatives have the following structural formula: [0004] Wherein R can be any one of aliphatic hydrocarbon group, aryl group, aralkyl group, halogen, ester group, acyloxy group, amide group, alkoxy group, etc., preferably aralkyl group with 6-9 carbon numbers, Any one of chlorobromo substituents, acyloxy groups with 1-4 carbon atoms, carboxamide groups, methoxy groups or ethoxy g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/06C07C45/28C07C47/24C07C47/232C07C67/29C07C69/07C07C69/145C07C47/277C07C231/12C07C233/31
CPCC07B41/06C07C45/28C07C67/29C07C231/12C07C47/24C07C47/232C07C69/07C07C69/145C07C47/277C07C233/31
Inventor 张红涛张永振刘英俊庞计昌崔娇英黎源华卫琦
Owner WANHUA CHEM GRP CO LTD
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