Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Oxidation of Benzylic Alcohols with Urea Hydrogen Peroxide/Calcium Chloride in PEGDME250

  • Received : 2013.08.01
  • Accepted : 2013.11.09
  • Published : 2014.02.20
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Abstract

Keywords

Experimental

All the alcohols and PEGDME250 were purchased from Aldrich and used as received. The reactions were checked by TLC using silica gel plates. Merck silica gel 60 (230-400 mesh) was used for flash column chromatography. 1H NMRspectra were measured by the Varian Gemini 2000 (300MHz) spectrometer tetramethylsilane as an internal standard and CDCl3 as a solvent. Mass spectra were recorded with a Micromass Autospectrometer. All products were known and identified by comparison of their 1H NMR spectra with those of reported literature data.

General Procedure. A mixture of benzylic alcohol (1.0 mmol), urea hydrogen peroxide (1.5 mmol) and calcium chloride (0.5 mmol) was stirred in PEGDME250 (2 mL) at 70 oC for 4 h. After cooling the mixture to room temperature the product is extracted into diethyl ether (3 × 20 mL), washed with water and dried over MgSO4. The combined ether extracts were concentrated under reduced pressure and the crude product was purified by flash column chromatography (ethyl acetate/n-hexane = 1:3, v/v) to give the desired carbonyl compound.

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