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Preparation method of 1-adamantyl methy ketone

A technology of adamantane methyl ketone and adamantane carboxylic acid, which is applied in the field of preparation of 1-adamantane methyl ketone, can solve the problems of low yield, achieve cost reduction, facilitate post-processing, and protect the environment

Inactive Publication Date: 2019-05-28
PANJIN GELIN KAIMO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The synthetic route uses adamantane as a raw material, first prepares 1-bromoadamantane, reacts with acetylene gas in the presence of concentrated sulfuric acid, and then hydrolyzes to obtain the intermediate 1-adamantanyl methyl ketone. Although there are few reaction steps, Yield is too low

Method used

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  • Preparation method of 1-adamantyl methy ketone

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Comparison scheme
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Embodiment 1

[0019] A preparation method for 1-adamantyl methyl ketone, comprising the steps of:

[0020] Step 1: In the reaction flask, add 2.5mol adamantane and 4.5mol liquid bromine in sequence, heat up at 80-90°C for 6h, then react at 110-115°C (oil temperature) for 3h, and let stand overnight. Recover 30 mL of bromine by distillation, then reduce the remaining bromine with saturated sodium bisulfite solution (200 mL), filter, wash the filter cake with water until neutral, dry, and recrystallize from methanol to obtain 470 g of light yellow crystalline 1-bromoadamantane, yield : 92.7%, mp117-119℃;

[0021] Step 2: In a 1000mL flask, add 98.4% concentrated sulfuric acid (500mL), start stirring, at about 5-10°C, add 0.1mol 1-bromoadamantane, 50mL n-hexane, stir rapidly, add dropwise 45mL formic acid, After 1 hour of dripping, keep the temperature at 5-10°C and react for 3 hours. Pour the reaction solution into ice water to obtain a mixture of ice and water (1500 mL), let it stand, filt...

Embodiment 2

[0026] A preparation method for 1-adamantyl methyl ketone, comprising the steps of:

[0027] Step 1: Add 2.5 mol of adamantane and 4.9 mol of liquid bromine in sequence in the reaction flask, heat up at 80-90°C for 6 hours, then react at 110-115°C (oil temperature) for 3 hours, and let stand overnight. Recover 30 mL of bromine by distillation, then reduce the remaining bromine with saturated sodium bisulfite solution (200 mL), filter, wash the filter cake with water until neutral, dry, and recrystallize from methanol to obtain 470 g of light yellow crystalline 1-bromoadamantane, yield : 92.4%, mp117-119℃;

[0028] Step 2: In a 1000mL flask, add 98.4% concentrated sulfuric acid (500mL), start stirring, at about 5-10°C, add 0.1mol 1-bromoadamantane, 55mL n-hexane, stir rapidly, add 45mL formic acid dropwise, After 1 hour of dripping, keep the temperature at 5-10°C and react for 3 hours. Pour the reaction solution into ice water to obtain a mixture of ice and water (1500 mL), l...

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Abstract

The invention belongs to the field of preparation of chemical intermediates, and particularly relates to a preparation method of 1-adamantyl methy ketone. The preparation method comprises the following steps of step 1, enabling adamantane and liquid bromine to react, so as to obtain 1-bromoadamantane; step 2, using concentrated sulfuric acid as a catalyst, adding the 1-bromoadamantane and n-hexane, and dripping formic acid, so as to obtain 1-adamantanecarboxylic acid; step 3, enabling the 1-adamantanecarboxylic acid and thionyl chloride to react, heating and refluxing, extracting by benzene, and directly applying the extracting liquid for the reaction in next step; step 4, dripping a mixed solution of benzene, diethyl malonate and anhydrous ethyl alcohol into a mixed solution of magnesiumpowder, iodine, anhydrous ethyl alcohol and benzene, dripping a benzene solution of 1-adamantanecarbonyl chloride, extracting by benzene, drying and distilling, so as to obtain 2- adamantanecarbonyl diethyl malonate; step 5, adding glacial acetic acid, water and concentrated sulfuric acid into the residue. The preparation method has the advantage that the yield rate is high.

Description

technical field [0001] The invention belongs to the field of preparation of chemical intermediates, and in particular relates to a preparation method of 1-adamantyl methyl ketone. Background technique [0002] Riantadine hydrochloride is used to synthesize antiviral drugs. Its antiviral effect is similar to amantadine, but its antiviral spectrum is wider, and its anti-A2 virus, parainfluenza virus and other effects are better than amantadine. For the prevention of Asian A2 influenza virus infection, the curative effect is better than amantadine. 1-Adamantyl methyl ketone is an intermediate in the synthesis of traditional Chinese medicine from rimantadine hydrochloride. At present, the synthetic route in the literature is as follows: [0003] [0004] The synthetic route uses adamantane as a raw material, first prepares 1-bromoadamantane, reacts with acetylene gas in the presence of concentrated sulfuric acid, and then hydrolyzes to obtain the intermediate 1-adamantanyl m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/67C07C49/323
Inventor 宫宁瑞
Owner PANJIN GELIN KAIMO TECH CO LTD
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