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Method for preparing 1-(2, 6, 6-trimethyl-3-cyclohexenyl)-1, 3-butanedione

A technology of cyclohexenyl and trimethyl, applied in the field of preparation of 1--1,3-butanedione, can solve problems such as low yield

Active Publication Date: 2015-07-08
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

[0005] However, the above-mentioned prior art produces 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione in a relatively low yield

Method used

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  • Method for preparing 1-(2, 6, 6-trimethyl-3-cyclohexenyl)-1, 3-butanedione
  • Method for preparing 1-(2, 6, 6-trimethyl-3-cyclohexenyl)-1, 3-butanedione

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preparation example Construction

[0022] The invention provides a preparation method of 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione, comprising the following steps:

[0023] React 1-(2,6,6-trimethylcyclohex-3-enyl)ethanone with an acetylating reagent in a solvent to obtain 1-(2,6,6-trimethylcyclohex-3-enyl) Hexenyl)-1,3-butanedione.

[0024] The present invention uses 1-(2,6,6-trimethylcyclohex-3-enyl)ethanone as raw material, and its structural formula is shown in formula II:

[0025]

[0026] The present invention has no special restrictions on the source of the (2,6,6-trimethylcyclohex-3-enyl)ethanone, using 1-(2,6,6-trimethyl Cyclohex-3-enyl)ethanone can be used. In a specific embodiment of the present invention, the preparation method disclosed in the patent application number 200710071156.9 is preferably used for preparation.

[0027] In the present invention, the acetylation reagent preferably includes one or more of acetyl chloride, acetic anhydride and glacial acetic acid. In the present ...

Embodiment 1

[0041] Add 300mL xylene and 46.8g (1.2mol) sodium amide to the reaction flask, adjust the temperature to 50°C, and add 166g (1.0mol) 1-(2,6,6-trimethylcyclohexyl-3- Alkenyl) ethyl ketone, the temperature is controlled at 50°C, and the drop is completed in about 2 hours. After the dropwise addition, continue to react at a constant temperature of 50°C for 0.5 hours, the reaction solution is cooled to 30°C, and 184g (1.8mol) of acetic anhydride is slowly added dropwise, and the reaction The temperature is controlled at 30°C, the dropwise addition is completed in about 2 hours, and the constant temperature reaction is continued for 1 hour;

[0042]Slowly add 500mL of water to the obtained reaction solution, stir completely and then separate into layers, then add 300mL of 10% sulfuric acid, stir completely and then separate into layers, neutralize the oil layer with 3% sodium hydroxide solution to neutrality, then add 300mL of water to wash; The solvent was recovered, rectified und...

Embodiment 2

[0050] Add 200mL toluene and 24g (1.0mol) sodium hydride to the reaction flask, adjust the temperature to 30°C, and add 166g (1.0mol) 1-(2,6,6-trimethylcyclohex-3-enyl) dropwise under stirring ) ethyl ketone, the temperature is controlled at 30°C, and the drop is completed in about 3 hours. After the dropwise addition, continue to react at a constant temperature of 30°C for 1 hour. At 20°C, the dropwise addition is completed in about 3 hours, and the constant temperature reaction is continued for 2 hours;

[0051] Slowly add 500mL of water to the obtained reaction solution, stir completely and separate layers, then add 300mL of 2% phosphoric acid, stir completely and separate layers, the oil layer is neutralized to neutral with 3% potassium hydroxide solution, and then washed with 300mL of water. Recover the solvent, rectify under reduced pressure, collect the fraction at 95-96°C / 2mmHg, and obtain 172.3g of light yellow transparent oily liquid; the light yellow transparent oil...

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Abstract

The invention discloses a method for preparing 1-(2, 6, 6-trimethyl-3-cyclohexenyl)-1, 3-butanedione. The method comprises the following steps: reacting 1-(2, 6, 6-trimethyl hexamethylene-3-alkenyl) butanone and an acetylation reagent in a solvent to obtain the 1-(2, 6, 6-trimethyl-3-cyclohexenyl)-1, 3-butanedione. By taking 1-(2, 6, 6-trimethyl hexamethylene-3-alkenyl) butanone as a raw material, the prepared 1-(2, 6, 6-trimethyl-3-cyclohexenyl)-1, 3-butanedione has high yield. The experiment result shows that the content of the obtained 1-(2, 6, 6-trimethyl-3-cyclohexenyl)-1, 3-butanedione is 97.5% and the yield is 93.1%. The product prepared by the method is faint yellow or colorless and transparent oily liquid and can be directly used for modulating an essence.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a preparation method of 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione. Background technique [0002] The CAS number of 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione is 771563-70-3, and its structural formula is shown in Formula I. It is an important aroma-inducing component in tobacco, as long as a small amount is added, it can make the cigarette smoke more like the aroma of well-modulated and mature tobacco. [0003] [0004] In 2003, Deng Changjian et al. published a study on the synthesis of 3-hydroxy-1-(2,6,6-trimethyl-3-cyclohexenyl)-1-butanone and its release of δ-turkone into cigarette smoke. "It is mentioned that 4-acetyl-3,5,5-trimethylcyclohexene reacts with ethyl acetate in the presence of toluene and self-made sodium ethoxide to obtain 1-(2,6,6-trimethyl- 3-cyclohexenyl)-1,3-butanedione, the color of the product is yellowish brown,...

Claims

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Application Information

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IPC IPC(8): C07C49/543C07C45/72
CPCC07C45/455C07C2601/16C07C49/543
Inventor 叶剑飞林传明黄旺生彭彩红王盈华李志江胡建良范宇鹏
Owner 格林生物科技股份有限公司