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Synthetic method for organic synthesis intermediate 4-methylcyclohexanone

A technology for methylcyclohexanone and organic synthesis, applied in the preparation of organic compounds, organic chemistry, chemical instruments and methods, etc., can solve the problem of increased corrosion resistance requirements for reaction equipment, increased risk factors in the synthesis process, and complex synthesis processes and other problems, so as to avoid the increase of corrosion resistance requirements, shorten the reaction time and improve the reaction yield

Inactive Publication Date: 2018-07-03
CHENGDU KA DI FU TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This synthesis method needs to maintain a low temperature environment, generally about 0°C, and the energy consumption required for the reaction is relatively high, which is not conducive to reducing the reaction cost, and the free chlorine gas released by sodium hypochlorite can cause poisoning and skin diseases, and its solution is corrosive. It can damage the skin. Production personnel should wear work clothes, gas masks, latex gloves, rubber aprons, and long rubber boots to protect the respiratory organs and skin. These will increase the cost of the reaction and increase the risk factor of the synthesis process. , is not conducive to reducing engineering costs, and the strong corrosiveness of sodium hypochlorite solution will also lead to an increase in the corrosion resistance requirements of reaction equipment, resulting in a further increase in production costs, and the entire synthesis process is relatively complicated, so it is necessary to propose a new synthesis method

Method used

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  • Synthetic method for organic synthesis intermediate 4-methylcyclohexanone
  • Synthetic method for organic synthesis intermediate 4-methylcyclohexanone
  • Synthetic method for organic synthesis intermediate 4-methylcyclohexanone

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Experimental program
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Effect test

Embodiment 1

[0017] The synthetic method of organic synthesis intermediate 4-methylcyclohexanone comprises the steps:

[0018] A: Add 3mol 1-methoxy-4-methyl-6-bromocyclohexane in the reaction vessel, 900ml of sulfolane solution with a mass fraction of 20%, increase the solution temperature to 10°C, and add a mass fraction of 10% oxalic acid solution to adjust the pH of the solution to 5, then add 6mol potassium peroxodisulfate, and continue the reaction for 90min;

[0019] B: Then raise the temperature to 20°C, add 6mol mass fraction of 15% potassium chloride solution, 6mol phenylmercury acetate, continue the reaction for 1h, separate the layers of the solution, separate the oil layer, and use a 50% mass fraction of sodium nitrate solution Wash for 30 minutes, wash with 80% hexanoic acid solution for 20 minutes, recrystallize in 85% cyclohexanone solution, and dehydrate with anhydrous sodium sulfate to obtain 329.952 g of finished product 4-methylcyclohexanone. The rate is 98.2%.

Embodiment 2

[0021] The synthetic method of organic synthesis intermediate 4-methylcyclohexanone comprises the steps:

[0022] A: Add 3mol 1-methoxy-4-methyl-6-bromocyclohexane in the reaction vessel, 900ml of sulfolane solution with a mass fraction of 23.5%, increase the solution temperature to 12.5°C, and add a mass fraction of 13% oxalic acid solution to adjust the pH of the solution to 5.25, then add 7mol potassium peroxodisulfate, and continue the reaction for 110min;

[0023] B: Then raise the temperature to 22°C, add 7mol mass fraction of 18.5% potassium chloride solution, 7mol phenylmercury acetate, continue the reaction for 1.5h, separate the layers of the solution, separate the oil layer, and use a mass fraction of 53% sodium nitrate The solution was washed for 40 minutes, and the hexanoic acid solution with a mass fraction of 83% was washed for 30 minutes, recrystallized in a cyclohexanone solution with a mass fraction of 88.5%, and dehydrated with anhydrous sodium sulfate as a ...

Embodiment 3

[0025] The synthetic method of organic synthesis intermediate 4-methylcyclohexanone comprises the steps:

[0026] A: Add 3mol 1-methoxy-4-methyl-6-bromocyclohexane in the reaction vessel, 900ml of sulfolane solution with a mass fraction of 27%, increase the solution temperature to 15°C, and add a mass fraction of 16% oxalic acid solution to adjust the pH of the solution to 5.5, then add 8mol potassium peroxodisulfate, and continue the reaction for 130min;

[0027] B: Then raise the temperature to 24°C, add 8 mol of potassium chloride solution with a mass fraction of 22%, and 8 mol of phenylmercury acetate, continue to react for 2 hours, separate the layers of the solution, separate the oil layer, and use a 56% sodium nitrate solution Wash for 50 minutes, wash with 86% hexanoic acid solution for 40 minutes, recrystallize in a 92% cyclohexanone solution, and dehydrate with anhydrous sodium sulfate to obtain 331.632 g of finished product 4-methylcyclohexanone. The rate is 98.7%....

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Abstract

The invention discloses a synthetic method for the organic synthesis intermediate 4-methylcyclohexanone. The synthetic method comprises the following steps: adding 1-methoxy-4-methyl-6-bromocyclohexane and a sulfolane solution into a reaction vessel, raising a solution temperature, adding an oxalic acid solution to adjust the pH value of the obtained solution, then adding potassium peroxodisulfate, and continuing a reaction; and then raising the temperature, adding a potassium chloride solution and phenylmercuric acetate, continuing the reaction, subjecting the obtained solution to layering, separating an oil layer, washing the oil layer with a sodium nitrate solution at first and then with a hexanoic acid solution, carrying out recrystallization in a cyclohexanone solution, and then carrying out dehydration with a dehydrating agent to obtain the finished 4-methylcyclohexanone.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, belonging to the field of organic synthesis, in particular to a synthesis method of an organic synthesis intermediate 4-methylcyclohexanone. Background technique [0002] 4-Methylcyclohexanone is mainly used as an intermediate of cyclonitrosourea. Cyclonitrosourea is mainly used for malignant lymphoma, brain tumor, melanoma, lung cancer, etc., and has a good curative effect. Most of the existing synthetic methods of 4-methylcyclohexanone adopt 4-methylcyclohexanol, TEMPO, and sodium hypochlorite as reactants to generate products. This synthesis method needs to maintain a low temperature environment, generally about 0°C, and the energy consumption required for the reaction is relatively high, which is not conducive to reducing the reaction cost, and the free chlorine gas released by sodium hypochlorite can cause poisoning and skin diseases, and its solution is corrosive. I...

Claims

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Application Information

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IPC IPC(8): C07C49/403C07C45/61C07C45/27C07C49/463
CPCC07C45/27C07C45/61C07C49/463C07C49/403
Inventor 廖如佴
Owner CHENGDU KA DI FU TECH
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