A New and Efficient Transition Metal-Free Oxidation of Secondary Alcohols to Ketones Using Aqueous HBr and H₂O₂

Abstract

Aqueous HBr/H₂O₂ was found to be an efficient and green system for the oxidation of secondary alcohols in excellent yields under very mild conditions.

Key words

oxidation - secondary alcohols - ketones

References

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19

General Experimental Procedure: To a stirred solution of secondary alcohol (1 mmol) and 30% H₂O₂ (2 mmol) in MeCN (5 mL) was added drop wise aq 48% HBr (20 mol%) and the reaction mixture was refluxed for the time as given in Table [1] . The progress of the reaction was monitored by TLC (SiO₂). At the end of reaction the excess H₂O₂ was destroyed by the addition of aq bisulfite followed by the filtration through a small Buchner funnel. After filtration, the reaction mixture was purified by the solvent extraction with CH₂Cl₂ (3 times) and the solvent was evaporated under vacuum. The residue thus obtained was purified by column chromatography on silica gel using EtOAc-hexane (1:4) as eluent. Evaporation of the solvent yielded corresponding ketones. The reaction times and yields of the products are presented in the Table [1] . The products were identified by comparing their physical and spectral data with those of authentic compounds reported in literature.