Silver nitrate-catalyzed oxidation of aldehydes to carboxylic acids by H2O2

Tetrahedron Letters

Volumn 50, Issue 47, 2009, Pages 6553-6556

  Chakraborty, Debashis ^a   Gowda, Ravikumar R ^a   Malik, Payal ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Aldehyde; Carboxylic acid; Oxidation

Indexed keywords

ALDEHYDE; BENZALDEHYDE; BENZOIC ACID; CARBOXYL GROUP; HYDROGEN PEROXIDE; SILVER NITRATE;

ARTICLE; CATALYSIS; CONCENTRATION (PARAMETERS); OXIDATION; OXIDATION KINETICS; REACTION OPTIMIZATION; REACTION TIME;

EID: 77954244930     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.044     Document Type: Article

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40. Typical experimental procedure: To a stirred solution of AgNO3 (16.99 mg, 0.1 mmol) and aldehyde (1 mmol) in 2 mL MeCN was added 30% H2O2 (0.57 mL, 5 mmol). The reaction mixture was slowly heated to 50 °C. The progress of the reaction was monitored using TLC until all aldehyde was found consumed. The reaction was quenched with cold 10% Na2S2O3 solution and extracted with dichloromethane. All the volatiles were removed to yield the crude product. The crude product was treated with saturated NaHCO3 solution. This was extracted with dichloromethane. Finally, the aqueous layer was acidified using 2 N HCl and extracted with dichloromethane. The organic layer was concentrated and subjected to column chromatography. Comparable yields and purity of the products were obtained employing ethyl acetate as an alternative solvent for work-up. The spectral data of the various carboxylic acids were found to be satisfactory in accord with the literature.