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Synlett 2018; 29(07): 974-978
DOI: 10.1055/s-0037-1609149
DOI: 10.1055/s-0037-1609149
letter
Sulfuric Acid-Promoted Oxidation of Benzylic Alcohols to Aromatic Aldehydes in Dimethyl Sulfoxide: An Efficient Metal-Free Oxidation Approach
This research was supported by the Research Council of University of Tehran.Further Information
Publication History
Received: 17 October 2017
Accepted after revision: 18 December 2017
Publication Date:
29 January 2018 (online)
Abstract
An efficient metal-free oxidation of benzylic alcohols to aromatic aldehydes is described. Heating a solution of the benzylic alcohol in DMSO in the presence of H2SO4 afforded the corresponding aldehyde in excellent yield. This oxidation reaction, which proceeds with a short reaction time and no side products, is akin to the Pfitzner–Moffatt oxidation, but without the need for N,N′-dicyclohexylcarbodiimide.
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- 22 Aldehydes 2a–n; General Procedures Protocol A: A mixture of the benzylic alcohol 1 (1 mmol) and 98% H2SO4 (1 mmol) in DMSO (3 mL) was stirred for the appropriate time under reflux conditions. The mixture was then cooled to r.t., and brine (4 mL) was added. The organic phase was extracted with CH2Cl2 (6 mL), and the organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. In all cases, the reaction products were obtained with high purity, and did not require further purification by distillation or column chromatography. Protocol B: A mixture of benzylic alcohol (1 mmol) and 98% H2SO4 (0.5 mmol) in DMSO (3 mL) was stirred for the appropriate reaction time under reflux conditions. The reaction mixture was then worked up as described in Protocol A.