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1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-1,3-butadiene and preparation method thereof

A technology of cyclohexene and methoxy, which is applied in the field of intermediate 1-methoxy-2-methyl-4--1, can solve the problems of poor atom economy, achieve low cost, easy to obtain raw materials, and advanced technology The effect of simple route

Inactive Publication Date: 2015-03-18
SHAOXING UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The method requires a large excess of methyl chloroacetate and a basic condensing agent, with poor atom economy

Method used

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  • 1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-1,3-butadiene and preparation method thereof
  • 1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-1,3-butadiene and preparation method thereof
  • 1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-1,3-butadiene and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1: Preparation of 1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1,3-butadiene

[0031] Add potassium tert-butoxide (12.3g, 0.11mol) and a mixture of tetrahydrofuran and dimethyl sulfoxide (50mL, 8:1, V / V) into a 250mL three-neck flask protected by nitrogen, keep it warm in a cold bath, and stir mechanically Then, add the phosphonate (24.4g, 0.11mol) shown in formula III dropwise, keep at -20°C for about half an hour to complete the dropwise addition, continue to keep warm and stir for about 1 hour to make the carbanion dissociation reaction fully; then keep at -20°C Add α-cyclocitral (15.2g, 0.1mol) represented by formula II dropwise, and the dropwise addition is completed in about 1 hour. Continue to keep warm and stir for about half an hour. After the reaction is completed by gas chromatography, add water (50mL) and diethyl ether (100mL) Stir for 10 minutes, separate layers, wash the ether layer with 5% aqueous sodium chloride solution (25mL*3), dry...

Embodiment 2～8

[0037] Examples 2-8: Condensation reactions under different bases, solvents and reaction temperatures to prepare 1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexene- 1-yl)-1,3-butadiene

[0038] Add a certain amount of alkali and 20mL of a certain solvent into a 250ml three-necked flask protected by nitrogen gas (see Table 1 for the types of alkali and solvent), keep it warm in a cold bath, and add a certain amount of phosphine shown in formula III dropwise under mechanical stirring. 20mL of the above-mentioned solvent of the acid ester (see Table 1 for the molar amount), kept at a certain temperature for about half an hour to complete the dropwise addition, and continued to insulate and stir for about 1 hour to make the carbanion dissociation reaction fully; then keep the above temperature, dropwise added The above solvent of α-cyclic citral (7.6g, 0.05mol) was added dropwise in about 1 hour, and continued to keep stirring at the above temperature for about half an hour. Afte...

Embodiment 9

[0049] Example 9: Preparation of 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butene-1-aldehyde

[0050] Add the 1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl) prepared in Example 1 to the 250mL three-necked flask protected by nitrogen -1,3-butadiene (11.0g, 0.05mol), tetrahydrofuran (100g) and p-toluenesulfonic acid (0.7g), stir well, add water (22g) dropwise, and stir at 20-25°C for 24 hours, Gas chromatographic tracking reaction is basically complete, add a solution configured by 2g sodium bicarbonate and 20g water to neutralize, steam the tetrahydrofuran under reduced pressure with a water pump, then add 100mL cyclohexane, separate layers, and the organic layer is washed with 30mL water After drying with magnesium sulfate over water, the solvent was recovered under reduced pressure to obtain the crude product of 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butene-1-aldehyde 10.1g, GC content 73.1%, yield is 71.7%.

[0051] The structure of the product i...

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Abstract

The invention provides an enol ether 1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-1,3-butadiene shown in a formula I and a preparation method thereof. In the presence of an acid catalyst, the 1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-1,3-butadiene is subjected to hydrolysis reaction to prepare 2-methyl-4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-2-butene-1-aldehyde. The process line is simple, easily available in raw materials and low in cost, and has industrial value.

Description

technical field [0001] The present invention relates to a kind of intermediate 1-methoxy-2-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1,3-butadiene and its preparation method. Background technique [0002] 2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butene-1-aldehyde, its molecular structure is shown in formula IV, it is perfume and An important carotenoid intermediate. The synthesis of 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butene-1-aldehyde is mainly based on the α-ionone shown in formula V As a raw material, it is prepared by Darzens condensation with methyl chloroacetate in the presence of an alkaline condensing agent, followed by hydrolysis and decarboxylation. The reaction equation is as follows: [0003] [0004] This method requires a large excess of methyl chloroacetate and a basic condensing agent with poor atom economy. Contents of the invention [0005] In order to overcome the defects in the above-mentioned prior art, the object of the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/162C07C41/01C07C47/225C07C45/42
CPCC07C41/30C07C45/42C07C2601/16C07C43/162C07C47/225
Inventor 沈润溥吕春雷曹瑞伟盛国栋宋小华陈斌陈朝辉吴春雷
Owner SHAOXING UNIVERSITY
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