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Method for synthesizing o-nitroacetophenone compound

A technology of nitroacetophenone and compounds, which is applied in the field of synthesis of organic compounds, can solve problems such as psychological pressure, inconvenient operation, and toxicity of raw materials, and achieve the effects of good substrate adaptability, simple reaction steps, and good selectivity

Inactive Publication Date: 2013-05-29
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials used in the inventive method are toxic, and protective measures are required during use, which brings inconvenience to the operation and brings psychological pressure to the operator.

Method used

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  • Method for synthesizing o-nitroacetophenone compound
  • Method for synthesizing o-nitroacetophenone compound
  • Method for synthesizing o-nitroacetophenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Using acetophenone as raw material

[0038]

[0039] (2) Add 0.600 g (5.0 mmol) of acetophenone, 0.414 g (6.0 mmol) of hydroxylamine hydrochloride, 0.492 g (6.0 mmol) of anhydrous sodium acetate and 3 ml of methanol into a 25 ml flask. After the mixture was heated to reflux for 2 hours, TLC detected that the reaction was complete. After adding 15 ml of ethyl acetate for dilution, the solids in the mixed solution were dissolved with 2 N sodium hydroxide solution. The resulting mixed solution was extracted with ethyl acetate, dried and removed under reduced pressure. solvent to obtain 0.641 g (95% yield) of light yellow solid acetophenone oxime.

[0040] (3) The volume ratio of the obtained light yellow solid acetophenone oxime to DMSO:H 2 O = 1:1 solution was dissolved, 2.5 g potassium hydroxide (0.5 g × 5) and 0.852 g (6.0 mmol) methyl iodide were added, and stirred at room temperature for 3 hours. After the reaction was detected by TLC, the reaction solution w...

Embodiment 2

[0045] (1) Using 4-fluoroacetophenone as raw material

[0046]

[0047] (2) Add 0.690 g (5.0 mmol) of 4-fluoroacetophenone, 0.414 g (6.0 mmol) of hydroxylamine hydrochloride, 0.492 g (6.0 mmol) of anhydrous sodium acetate and 3 ml of methanol into a 25 ml flask. After the mixture was heated to reflux for 2 hours, TLC detected that the reaction was complete. After adding 15 ml of ethyl acetate for dilution, the solids in the mixed solution were dissolved with 2 N sodium hydroxide solution. The resulting mixed solution was extracted with ethyl acetate, dried and removed under reduced pressure. solvent to obtain 0.734 g (96% yield) of 4-fluoroacetophenone oxime as a pale yellow solid.

[0048] (3) The obtained light yellow solid 4-fluoroacetophenone oxime was mixed with the volume ratio DMSO:H 2 O = 1:1 solution was dissolved, 2.5 g potassium hydroxide (0.5 g × 5) and 0.852 g (6.0 mmol) methyl iodide were added, and stirred at room temperature for 3 hours. After the reaction...

Embodiment 3

[0053] (1) Using 4-chloroacetophenone as raw material

[0054]

[0055] (2) Add 0.770 g (5.0 mmol) of 4-chloroacetophenone, 0.414 g (6.0 mmol) of hydroxylamine hydrochloride, 0.492 g (6.0 mmol) of anhydrous sodium acetate and 3 ml of methanol into a 25 ml flask. After the mixture was heated to reflux for 2 hours, TLC detected that the reaction was complete. After adding 15 ml of ethyl acetate for dilution, the solids in the mixed solution were dissolved with 2 N sodium hydroxide solution. The resulting mixed solution was extracted with ethyl acetate, dried and removed under reduced pressure. solvent to obtain 0.811 g (96% yield) of 4-chloroacetophenone oxime as a pale yellow solid.

[0056] (3) The obtained light yellow solid 4-chloroacetophenone oxime was mixed with DMSO:H 2 O = 1:1 solution was dissolved, 2.5 g potassium hydroxide (0.5 g × 5) and 0.852 g (6.0 mmol) methyl iodide were added, and stirred at room temperature for 3 hours. After the reaction was detected by ...

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Abstract

The invention provides a method for synthesizing o-nitroacetophenone compound, relating to a method for synthesizing organic compound. The invention takes acetophenone (can contain various substituent groups) as raw material directly, carbonyl group is converted into hydroxyimino, then palladium is taken as catalyst, carbon-hydrogen bond activation single nitration on the adjacent position of hydroxyimino is realized in the presence of oxidant and nitration agent, and finally hydroxyimino is hydrolyzed into corresponding ketone again under the action of acid, thus realizing nitration of adjacent position of carbonyl group of acetophenone and obtaining a series of o-nitroacetophenone compounds. The invention is safe and environmentally friendly, no waste gas or waste water is produced; adaptability of substrate is good, adjacent position nitration on various substituent groups can be realized; regioselectivity of nitration reaction is good; various nitroacetophenones are directly takenas raw materials, and reaction process is simple, thus being a new approach for synthesizing o-nitroacetophenone compound containing substituent groups.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for preparing an o-nitroacetophenone compound. Background technique [0002] O-nitroacetophenone compounds are important pharmaceutical intermediates and are also used as sensitizers for photosensitive resins, and are widely used in the chemical industry. At present, o-nitroacetophenone is mainly obtained from ethylbenzene through nitration, oxidation and other steps, but the nitration involved in the process is a traditional nitration method (mixed acid nitration method) that requires excessive amounts of strong acids such as nitric acid and sulfuric acid as a reaction Reagents and catalysts release a large amount of heat during the reaction, which is likely to cause production hazards. At the same time, a large amount of waste gas and acid are produced in this process, causing serious environmental problems. In addition, the problem of difficult-to-contro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/14C07C205/45
Inventor 刘运奎娄绍杰许丹倩徐振元
Owner ZHEJIANG UNIV OF TECH
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