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A method for preparing α-o-nitrophenylethanol by oxidation of o-nitroethylbenzene with catalyst-free oxygen

A technology of o-nitroethylbenzene and nitroethylbenzene, which is applied in the field of catalyst-free oxygen oxidation of o-nitroethylbenzene to prepare α-o-nitrophenylethanol, which can solve the difficulty of catalyst synthesis and the selection of α-o-nitrophenylethanol low yield, low conversion rate and yield, etc., to achieve the effect of cheap recycling, easy recycling and moderate reaction temperature

Active Publication Date: 2020-12-25
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This type of method solves the problems of equipment corrosion and environmental pollution in the preparation of α-o-nitrophenylethanol in acidic medium, but metalloporphyrins are also required as catalysts, because such catalysts have low synthesis yields, separation and purification Difficulty, need to consume a large amount of organic solvents and other problems; In addition, the reaction temperature is high; and what is generated is a mixture of alcohol and ketone acids, the selectivity and yield of α-o-nitrophenylethanol are all low, and the separation is difficult; making it industrially App is restricted
[0003] To sum up, whether it is the traditional reduction method of acetophenone derivatives or the biomimetic catalytic oxidation method, there are many problems, such as equipment corrosion, high production cost, heavy metal pollution, environmental pollution, difficulty in catalyst synthesis, conversion rate, etc. and low yields, which limit its industrial application

Method used

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  • A method for preparing α-o-nitrophenylethanol by oxidation of o-nitroethylbenzene with catalyst-free oxygen
  • A method for preparing α-o-nitrophenylethanol by oxidation of o-nitroethylbenzene with catalyst-free oxygen

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Effect test

Embodiment 1

[0024] Get o-nitroethylbenzene (907mg, 6mmol), sodium hydroxide (1.8g, 45mmol), add in 100ml autoclave, add methanol 10ml; After filling and changing oxygen three times, feed oxygen (pressure 1.8MPa), in oil bath The reaction was carried out at a temperature of 65° C. for 24 hours. After the reaction, add methanol for dilution, neutralize the pH value of the reaction mixture to 2-3, remove most of the solvent under reduced pressure, add ethyl acetate, dry and filter. After chromatographic column separation, 45 mg (0.30 mmol) of o-nitroethylbenzene was recovered, and the conversion rate of o-nitroethylbenzene was 95%, and 522 mg (3.12 mmol) of α-o-nitrophenylethanol was obtained, with a yield of 52%.

Embodiment 2

[0026] Get o-nitroethylbenzene (907mg, 6mmol), sodium hydroxide (1.8g, 45mmol), add in 100ml autoclave, add methanol 10ml; After filling and changing oxygen three times, feed oxygen (pressure 1.8MPa), in oil bath The reaction was carried out at a temperature of 65° C. for 24 hours. After the reaction, add methanol for dilution, neutralize the pH value of the reaction mixture to 4-5, remove most of the solvent under reduced pressure, add ethyl acetate, dry and filter. After chromatographic column separation, 27mg (0.18mmol) of o-nitroethylbenzene was recovered, and the conversion rate of o-nitroethylbenzene was 97%, and 702mg (4.20mmol) of α-o-nitrophenylethanol was obtained, with a yield of 70%.

Embodiment 3

[0028] Get o-nitroethylbenzene (907mg, 6mmol), sodium hydroxide (1.8g, 45mmol), add in 100ml autoclave, add methanol 10ml; After filling and changing oxygen three times, feed oxygen (pressure 1.8MPa), in oil bath The reaction was carried out at a temperature of 65° C. for 24 hours. After the reaction, add methanol for dilution, neutralize the pH value of the reaction mixture to 6-7, remove most of the solvent under reduced pressure, add ethyl acetate, dry and filter. After chromatographic column separation, 27.2mg (0.18mmol) of o-nitroethylbenzene was recovered, and the conversion rate of o-nitroethylbenzene was 97%, and 632mg (3.78mmol) of α-o-nitrophenylethanol was obtained, with a yield of 63%.

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Abstract

The invention discloses a method for preparing alpha-o-nitrophenylethanol through oxygen oxidation of o-nitroethylbenzene in absence of a catalyst and relates to a preparation method of alpha-o-nitrophenylethanol. The method comprises the following steps: under a condition that any catalyst is not added, by taking o-nitroethylbenzene as a raw material, taking oxygen as an oxidizing agent and taking sodium hydroxide as base, reacting in alcohol or an aqueous solution thereof at a reaction temperature of 25-65 DEG C; and performing after-treatment, separating and purifying, thereby obtaining thealpha-o-nitrophenylethanol. According to the method, any catalyst is not needed; the price of the raw material is low; the ethanol can serve as a solvent, is hardly toxic, cheap and easy to recover and reutilize; the reaction temperature is moderate, and production control is easy; the raw material conversion ratio is high; the target product is high in selectivity, has the yield of 88% and alsohas wide application prospects.

Description

technical field [0001] The invention relates to a preparation method of α-o-nitrophenylethanol, in particular to a method for preparing α-o-nitrophenylethanol by oxygen oxidation of o-nitroethylbenzene without a catalyst. Background technique [0002] α-Nitrophenylethanol is an important intermediate in organic synthesis, widely used in dyes, medicine, food, organic synthesis, photosensitive materials, textile industry and other fields. At present, the main method of synthesizing α-o-nitrophenylethanol is the reduction method of acetophenone derivatives (Organic Letters, 2005,7,1043; Photochemistry and Photobiology,2013,89,552; Chem Plus Chem,2013,78,1273; Eur .J.Org.Chem, 2015, 11, 2374; J.Org.Chem, 2016, 808, 68). However, there are very few reports on the preparation of α-o-nitrophenylethanol by oxidation of o-nitroethylbenzene. In 2011, Iranian scientist Fatemeh Rajabi and others reported that using o-nitroethylbenzene as a raw material, using silica-supported Co(II) a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/12C07C205/19
CPCC07C201/12C07C205/19
Inventor 佘远斌李贵杰方坤付海燕
Owner ZHEJIANG UNIV OF TECH
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