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Method for preparing 1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one

A technology of alkenyl and acetyl, which is applied in the field of preparation of 1-but-2-en-1-one, can solve the problems of low product yield, potential safety hazards, cumbersome operation, etc., and achieve high yield, simplified operation, The effect of less waste

Active Publication Date: 2010-05-26
格林生物科技股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The above two synthetic methods have problems such as cumbersome operation, low product yield, high cost, serious pollution, and potential safety hazards.

Method used

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  • Method for preparing 1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 24g (1mol) of magnesium powder and 250mL of tetrahydrofuran into the reaction flask, and feed in methyl chloride gas to prepare the methylmagnesium chloride Grignard reagent until the magnesium powder completely disappears. After cooling to room temperature, 166 g (1 mol) of 1-acetyl-2,6,6-trimethylcyclohex-3-ene was added dropwise. The reaction was exothermic and produced methane gas. The reaction temperature was controlled at 25°C, the dropwise was completed in about 4 hours, and the reaction was continued for 1 hour after the dropwise addition was completed. Cool to 5°C, slowly add 80g (1.8mol) of acetaldehyde dropwise, control the reaction temperature at 5°C, continue the reaction for 1h after the dropwise addition for about 6h.

[0025] The reaction was terminated with 600 mL of 20% sulfuric acid solution and dehydrated, and the organic phase was washed with 50 mL of 15% aqueous sodium hydroxide until neutral. After removing the solvent, rectify under reduced...

Embodiment 2

[0027] Add 24g (1mol) of magnesium powder and 250mL of tetrahydrofuran into the reaction flask, and feed methyl bromide gas to prepare methylmagnesium bromide Grignard reagent until the magnesium powder completely disappears. After completion, it was cooled to room temperature, and 166 g (1 mol) of 1-acetyl-2,6,6-trimethylcyclohex-3-ene was added dropwise. The reaction was exothermic, the reaction temperature was controlled at 28°C, the drop was completed in about 4 hours, and the reaction was continued for 1 hour after the dropwise addition was completed. Cool to 5°C, slowly add 60g (1.4mol) of acetaldehyde, control the reaction temperature at 10°C, drop it in about 6h, and continue the reaction for 1h.

[0028] The reaction was terminated with 650 mL of 15% sulfuric acid solution and dehydrated, and the organic phase was washed with 50 mL of 15% aqueous sodium hydroxide until neutral. After removing the solvent, rectify under reduced pressure, collect the fraction at 70-75°...

Embodiment 3

[0030] Add 24g (1mol) of magnesium powder and 250mL of tetrahydrofuran into the reaction flask, and feed ethyl chloride gas to prepare ethyl Grignard reagent until the magnesium powder disappears. After cooling to room temperature, 150 g (0.9 mol) of 1-acetyl-2,6,6-trimethylcyclohex-3-ene was added dropwise. The reaction temperature was controlled at 20°C, the drop was completed in about 4 hours, and the reaction was continued for 1 hour. Cool to 0°C, slowly add 65g (1.5mol) of acetaldehyde dropwise, control the reaction temperature at 5°C, drop it for about 6h, and continue the reaction for 1h.

[0031] The reaction was terminated with 1200 mL of 30% acetic acid solution and dehydrated, and the organic phase was washed with 100 mL of 15% sodium carbonate aqueous solution until neutral. Rectify under reduced pressure after removing the solvent, collect the fraction at 70~75℃ / 1mmHg to obtain 90g of 1-(2,6,6-trimethyl-cyclohex-3-enyl)but-2-en-1-one , yield 47%.

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Abstract

The invention relates to a preparation method of an organic compound, in particular to the preparation method of 1-(2, 6, 6-trimethyl hexanaphthene-3-alkylene) butyl-2-alkene-1-ketone. The method is that the 1-(2, 6, 6-trimethyl hexanaphthene-3-alkylene) butyl-2-alkene-1-ketone is prepared by adopting 1-acetyl-2, 6, 6-trimethyl hexanaphthene-3-alkene as raw material to be condensed and dehydratedwith aldehyde after the treatment of Grignard reagent. The invention has the advantages of simple operation, low cost, high productivity and little three wastes, etc., while the incense of the productwhich is prepared by the invention is up to the standard. The product of the invention has stronger flowery odour incense, excellent dispersion and low threshold value, and the invention can be slightly added into essence so as to greatly upgrade the incense of rose.

Description

technical field [0001] The invention belongs to the technical field of chemical industry and relates to a preparation method of 1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one. Background technique [0002] 1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one (trans-1-(2,6,6-trimethylcyclohex-3-enyl)but-2 -en-1-one) is a precious rose ketone series of spices, which has not been found in nature. It has a blackcurrant-like aroma, fruity aroma, and a natural aroma. It can be used in high-end daily chemical flavor formulations and food in spices. It has a strong floral aroma and good diffusing power, and the threshold is low. A small amount of it added to the essence can significantly enhance the aroma of roses. [0003] 1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one can be obtained from 1-acetyl-2,6,6-trimethylcyclohex-3-ene It can be obtained by condensation with acetaldehyde under alkaline conditions and dehydration. [0004] [0005] The raw material 1-acetyl-2,6,6-tri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/303C07C45/74
Inventor 尤坚萍白传伟胡建良陆文聪
Owner 格林生物科技股份有限公司
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