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Synthesis method of 4-hydroxy-2, 2, 6-trimethyl cyclohexanone

A technique for the synthesis of trimethylcyclohexanone, which is applied in the field of organic synthesis, can solve problems such as high difficulty in synthesis, difficulty in synthesis, and limited sources, and achieve the effects of reducing the difficulty of synthesis, increasing the total yield, and simplifying the synthesis route

Active Publication Date: 2022-02-25
WANHUA CHEM GRP CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the raw material 4-hydroxy-2,2,6-trimethylcyclohexanone is not easy to synthesize, and the source is limited
[0006] Tea aroma ketone, also known as 4-oxoisophorone, has a wide range of sources, using tea aroma ketone to prepare 4-hydroxy-2,2,6-trimethyl Cyclohexanone, and then the synthesis of Damascenone has significant advantages, but the preparation of 4-hydroxy-2,2,6-trimethylcyclohexanone from tea aroma ketone involves the selective reduction of ketone carbonyl, and the synthesis is difficult

Method used

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  • Synthesis method of 4-hydroxy-2, 2, 6-trimethyl cyclohexanone
  • Synthesis method of 4-hydroxy-2, 2, 6-trimethyl cyclohexanone
  • Synthesis method of 4-hydroxy-2, 2, 6-trimethyl cyclohexanone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) First, add 1521.2 g of tea aroma ketone, 15.2 g of 5% palladium-calcium carbonate catalyst, and 1500 g of ethanol to the autoclave, seal the autoclave, replace nitrogen for 3 times, press nitrogen to 3.0 MPa and confirm that the autoclave is well sealed , evacuate the nitrogen, replace with 2.0MPa hydrogen for 6 times, turn on the stirring paddle, keep the hydrogen pressure at 2.0MPa, and keep the inner temperature of the reactor at 60°C for 3h. After the stirring was stopped and the gas was released, the reaction liquid was analyzed by GC, and the composition of the reaction liquid was: 99.72% of 2,2,6-trimethyl-1,4-cyclohexanedione, 0.05% of tea aroma ketone, and 0.23% of others. The reaction solution was filtered, and ethanol was distilled off under reduced pressure at 90°C and 100 hPa to obtain 1543.3 g of crude 2,2,6-trimethyl-1,4-cyclohexanedione.

[0033] (2) Under an inert atmosphere, firstly mix 0.5mmol Rh(CO) 2 Dissolve acac in 5mL absolute ethanol, then ...

Embodiment 2

[0036](1) First, add 1521.2 g of tea aroma ketone, 8.0 g of 10% palladium-calcium carbonate catalyst, and 800 g of ethanol to the autoclave, seal the autoclave, replace nitrogen 3 times, press nitrogen to 6.0 MPa after confirming that the autoclave is well sealed , evacuate the nitrogen, replace with 5.0MPa hydrogen for 6 times, turn on the stirring paddle, keep the hydrogen pressure at 5.0MPa, and keep the inner temperature of the reactor at 70°C for 5 hours. After the stirring was stopped and the gas was released, the reaction liquid was analyzed by GC, and the composition of the reaction liquid was: 99.82% of 2,2,6-trimethyl-1,4-cyclohexanedione, 0.02% of tea aroma ketone, and 0.16% of others. The reaction solution was filtered, and ethanol was distilled off under reduced pressure at 90°C and 100 hPa to obtain 1543.5 g of crude 2,2,6-trimethyl-1,4-cyclohexanedione.

[0037] (2) Under an inert atmosphere, firstly mix 0.025mmol Rh 4 (CO) 12 Dissolve in 5mL absolute ethanol,...

Embodiment 3

[0040] (1) first add tea aroma ketone 1521.2g, 10% palladium-calcium carbonate catalyst 80g, ethanol 1000g to autoclave, autoclave is sealed, after nitrogen replacement 3 times, nitrogen stamping to 2.0MPa confirms that autoclave is well sealed, Evacuate the nitrogen, replace it with 1.0MPa hydrogen for 6 times, turn on the stirring paddle, keep the hydrogen pressure at 1.0MPa, and keep the inner temperature of the reactor at 80°C for 12 hours. After the stirring was stopped and the gas was released, the reaction liquid was analyzed by GC, and the composition of the reaction liquid was: 99.43% of 2,2,6-trimethyl-1,4-cyclohexanedione, 0.01% of tea aroma ketone, and 0.56% of others. The reaction solution was filtered, and ethanol was distilled off under reduced pressure at 90°C and 100 hPa to obtain 1543.6 g of crude 2,2,6-trimethyl-1,4-cyclohexanedione.

[0041] (2) Under an inert atmosphere, firstly mix 0.15mmol Rh 6 (CO) 16 Dissolve in 5mL absolute ethanol, then dissolve 1....

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Abstract

The invention provides a synthesis method of 4-hydroxy-2, 2, 6-trimethyl cyclohexanone, which comprises the following steps: (1) carrying out selective hydrogenation on tea flavor ketone under the action of a Lindlar catalyst to obtain 2, 2, 6-trimethyl-1, 4-cyclohexanedione, and (2) carrying out selective hydrogenation on 2, 2, 6-trimethyl-1, 4-cyclohexanedione to obtain 4-hydroxy-2, 2, 6-trimethyl cyclohexanone, wherein chiral rhodium is used as a hydrogenation catalyst in the step (2). The invention provides a new method for synthesizing the damascenone intermediate 4-hydroxy-2, 2, 6-trimethyl cyclohexanone, the operation is simple, the initial raw material tea flavor ketone is easy to obtain, and the 4-hydroxy-2, 2, 6-trimethyl cyclohexanone is high in yield and high in selectivity.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 4-hydroxy-2,2,6-trimethylcyclohexanone. Background technique [0002] Damascenone has an elegant rose aroma and is an important raw material for daily chemical flavors, and is used as a food flavor. Damascenone has many synthetic methods, one of which is the synthesis of damascenone from 4-hydroxy-2,2,6-trimethylcyclohexanone. [0003] Patents US4250332 and US3927107 report that 4-hydroxy-2,2,6-trimethylcyclohexanone undergoes acetylenation and rearrangement to obtain damascenone, and the hydroxyketone generated simultaneously in the reaction can be further dehydrated with phosphorus oxychloride to form large Horselenone. The reaction scheme is shown as follows: [0004] [0005] The route for synthesizing Damascenone from 4-hydroxy-2,2,6-trimethylcyclohexanone is streamlined, avoiding the need to use metal hydrides or Grignard reagents in other ro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/29C07C49/573
CPCC07C45/62C07C45/64C07C29/44C07C45/29C07C49/385C07C49/497C07C35/17C07C49/573
Inventor 鲍元野张永振黎源
Owner WANHUA CHEM GRP CO LTD
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