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Method for preparing 1-(2,6,6-trimethylcyclohex 3-alkenyl) ethyl ketone

A technology of trimethylcyclohexyl and alkenyl, applied in the field of preparation of 1-ethanone, can solve the problems of unqualified aroma, poor product selectivity, low yield, etc., and achieve improved product yield, high recycling rate, Good solubility effect

Inactive Publication Date: 2008-07-23
格林生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the above-mentioned organic solvent was applied to the Diels-Alder reaction of 1-(2,6,6-trimethylcyclohex-3-enyl)ethanone, the selectivity of the product was poor and the yield was low. , and a series of problems such as unqualified aroma

Method used

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  • Method for preparing 1-(2,6,6-trimethylcyclohex 3-alkenyl) ethyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 180g of nitroethane and 49g (0.5mol) of 4-methylpent-3-en-2-one into the reaction flask, stir well and then quickly add 50g (0.4mol) of anhydrous aluminum trichloride, and control the temperature for 5~ 20°C. After feeding, 125 g (1.8 mol) of 1,3-pentadiene was added dropwise, the reaction temperature was controlled at 25° C., the dropping time was controlled at 8 hours, and the reaction was continued for 3 hours after the dropwise addition was completed. The temperature dropped to 5°C, and washed with water until neutral. Recover the solvent and rectify under reduced pressure, collect the fraction at 78-82°C / 5mmHg to obtain 50 g of 1-(2,6,6-trimethylcyclohex-3-enyl)ethanone, with a yield of 60%.

Embodiment 2

[0021] Add 200g 1-nitropropane and 49g (0.5mol) 4-methylpent-3-en-2-one into the reaction flask, stir well and add 67g (0.5mol) anhydrous aluminum trichloride, control the temperature at 20°C . After feeding, 150 g (2.2 mol) of 1,3-pentadiene was added dropwise, the reaction temperature was controlled at 15° C., the dropping time was controlled at 10 h, and the reaction was continued for 3 h after the dropwise addition was completed. The temperature dropped to 5°C, and washed with water until neutral. Recover the solvent and rectify under reduced pressure, collect the fraction at 78-82°C / 5mmHg to obtain 58 g of colorless 1-(2,6,6-trimethylcyclohex-3-enyl)ethanone, with a yield of 70%.

Embodiment 3

[0023] Add 180g 2-nitropropane and 49g (0.5mol) 4-methylpent-3-en-2-one into the reaction flask, stir well and add 67g (0.5mol) anhydrous aluminum trichloride, control the temperature at 10°C . After feeding, 200 g (2.9 mol) of 1,3-pentadiene was slowly added dropwise, the reaction temperature was controlled at 18° C., the dropping time was controlled at 10 h, and the reaction was continued for 3 h after the dropwise addition was completed. The temperature dropped to 5°C, and washed with water until neutral. Recover the solvent and rectify under reduced pressure, collect the fraction at 78-82° C. / 5 mmHg to obtain 55 g of colorless 1-(2,6,6-trimethylcyclohex-3-enyl)ethanone with a yield of 66%.

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Abstract

The invention discloses a preparation method of organic compounds, in particular to 1- (2,6,6- trimethyl cyclohexyl - 3- alkenyl) ethyl ketone, which adopts 4- methyl amyl- 3- alkene - 2- alkone and 1,3- piperylenes as the raw material, with the anhydrous aluminum trichloride as the catalyst, and purifying and preparing through Diels-Alder reaction in the nitryl alkane solvent; wherein, the nitryl alkane solvent is one or several combination solvents among the nitroethane, 1- nitropropanes, and 2- nitropropanes, with a mass ratio of 3 to 5 times of 4- methyl amyl- 3- alkene -2- alkone. The preparation method of organic compounds has the advantages of using nitryl alkane as solvent, distinct enhancement of product efficiency, small solvent toxicity, good solubility, high recycling percentage, easy separation and purification of products, pure product fragrance, and other characteristics.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and specifically refers to a preparation method of 1-(2,6,6-trimethylcyclohex-3-enyl)ethanone. Background technique [0002] 1-(2,6,6-trimethylcyclohex-3-enyl)ethanone (1-(2,6,6-trimethylcyclohex-3-enyl)ethanone) is an important intermediate for the synthesis of rose ketone series of precious fragrances body. [0003] 1-(2,6,6-Trimethylcyclohex-3-enyl)ethanone is synthesized from 1,3-pentadiene and 4-methylpent-3-en-2-one usually by Diels-Alder reaction Prepared. [0004] [0005] The Diels-Alder reaction refers to the stereoselective cycloaddition of a diene or conjugated π-bonded molecule with an electron-donating group and a dienophile molecule with a stronger electron-withdrawing group to form a six-membered ring. into a reaction. [0006] Lewis acid has a strong catalytic effect on the Diels-Alder reaction, resulting in not only a fast reaction rate, but also better ...

Claims

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Application Information

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IPC IPC(8): C07C49/543C07C45/68
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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