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DOI: 10.1055/s-0028-1087391
Oxidation of Benzylic Alcohols with Urea-Hydrogen Peroxide and Catalytic Magnesium Bromide
Publication History
Publication Date:
12 December 2008 (online)
Abstract
Urea-hydrogen peroxide in the presence of a catalytic amount of magnesium bromide has been utilized efficiently for oxidation of primary and secondary benzylic alcohols into the corresponding aromatic aldehydes and ketones.
Key words
alcohols - hydrogen peroxide - ionic liquid - magnesium - urea
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References and Notes
General Experimental Procedure for the Oxidation of Benzylic Alcohols: To a solution of benzylic alcohol (1.0 mmol) and UHP (0.113 g, 1.2 mmol) in room-temperature ionic liquid, [bmim]BF4 (1 mL), was added MgBr2 (0.018 g, 0.1 mmol). The reaction mixture was stirred at 60 ˚C for 2-3 h and the reaction mixture was extracted with diethyl ether (2 × 5 mL). The combined diethyl ether layer was washed with sat. brine (2 × 5 mL) and dried with anhyd MgSO4. After evaporation of the solvent, the residue was purified by flash column chromatography (SiO2, hexane-EtAOc = 3:1) to afford pure carbonyl compound. The remaining ionic liquid was further washed with diethyl ether and reused in subsequent reactions.