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Method for synthesizing carboxylic acid or ketone compounds from alcohol or aldehyde by taking oxygen or oxygen in air as oxidant

A technology of ketone compounds and oxidants, which is applied in the direction of oxidative preparation of carbonyl compounds, preparation of organic compounds, organic chemical methods, etc., can solve the problem of low catalytic activity, and achieve the effects of environmental friendliness, high yield and mild reaction conditions

Active Publication Date: 2021-02-26
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In comparison, 4-hydroxy-2,2,6,6-tetramethylpiperidine oxide is extremely cheap, but its catalytic activity is very low

Method used

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  • Method for synthesizing carboxylic acid or ketone compounds from alcohol or aldehyde by taking oxygen or oxygen in air as oxidant
  • Method for synthesizing carboxylic acid or ketone compounds from alcohol or aldehyde by taking oxygen or oxygen in air as oxidant
  • Method for synthesizing carboxylic acid or ketone compounds from alcohol or aldehyde by taking oxygen or oxygen in air as oxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Add ferric nitrate nonahydrate (401.8mg, 1.0mmol), 4-hydroxy-2,2,6,6-tetramethylpiperidine oxide (172.4mg, 1.0mmol), potassium chloride (75.9mg , 1.0mmol), 1a (1.4381g, 10.0mmol) and 1,2-dichloroethane (2mL), pumped gas (pure oxygen) three times, stirred at room temperature (25°C) for 33 hours, and obtained 49% 2a (with dibromomethane as internal standard, NMR yield), 39% of 3a (with dibromomethane as internal standard, NMR yield).

Embodiment 2

[0034]

[0035] Add ferric nitrate nonahydrate (405.8mg, 1.0mmol), 4-hydroxy-2,2,6,6-tetramethylpiperidine oxide (171.4mg, 1.0mmol), potassium chloride (75.7mg , 1.0mmol), 1a (1.4353g, 10.0mmol) and dichloromethane (2mL), exchanged gas (pure oxygen) three times, and stirred at room temperature (25°C) for 33 hours to obtain 41% of 2a (based on dibromomethane Internal standard, NMR yield), 27% of 3a (with dibromomethane as internal standard, NMR yield).

Embodiment 3

[0037]

[0038] Add ferric nitrate nonahydrate (403.5mg, 1.0mmol), 4-hydroxy-2,2,6,6-tetramethylpiperidine oxide (171.6mg, 1.0mmol), potassium chloride (75.0mg , 1.0mmol), 1a (1.4359g, 10.0mmol) and toluene (2mL), gas exchanged (pure oxygen) three times, and stirred at room temperature (25°C) for 24 hours to obtain 25% of 2a (with dibromomethane as internal standard , NMR yield), 63% of 3a (with dibromomethane as internal standard, NMR yield).

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Abstract

The invention discloses a novel method for synthesizing a carboxylic acid or ketone compound from alcohol or corresponding aldehyde by taking oxygen or oxygen in air as an oxidant, which comprises thefollowing step of: oxidizing the alcohol or the corresponding aldehyde into the corresponding carboxylic acid or ketone compound under the catalysis of nitrate / 4hydroxy 2, 2, 6, 6-tetramethylpiperidine oxide and the action of an additive. When an inorganic chloride is additionally added, the reaction is accelerated. The method has the advantages that the catalyst is low in price, easy to operate,high in yield, rich in substrate diversity, mild in reaction condition, environmentally friendly and the like. The method is not only suitable for laboratory synthesis, but also suitable for industrial synthesis of carboxylic acid or ketone compounds.

Description

technical field [0001] The present invention relates to a kind of chemical synthesis method, specifically, it is a kind of new method that uses oxygen or the oxygen in the air as oxidant to synthesize carboxylic acid or ketone compound from alcohol or aldehyde, namely in nitrate, 4-hydroxyl-2 , Alcohols or aldehydes are oxidized to corresponding carboxylic acids or ketones in the presence of 2,6,6-tetramethylpiperidine oxide. Background technique [0002] Carboxylic acid is a kind of basic chemical raw material, which plays a pivotal role in the chemical industry. Oxidation reaction is the main synthesis route of carboxylic acid compounds. The environmental burden brought by traditional oxidation methods (heavy metal oxides) often becomes an insurmountable obstacle in industrial production. Therefore, the synthesis method based on air oxidation has attracted more and more attention. . In recent years, people have carried out some work in the air oxidation reaction field of...

Claims

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Application Information

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IPC IPC(8): C07C45/29C07C47/02C07C51/235C07C53/126C07C53/19C07C57/18C07C59/64C07C55/18C07C49/78C07C49/203
CPCC07C47/02C07C53/126C07C53/19C07C57/18C07C59/64C07C55/18C07C49/78C07C49/203C07C45/29C07C51/235C07C45/38C07C49/213C07C45/39C07B41/08C07B41/06C07C57/68C07C57/46
Inventor 麻生明刘金仙
Owner ZHEJIANG UNIV
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