N1C=CC=CC=1.[CH2:7]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:21])[CH2:18][CH:19]=[CH2:20])=[CH:13][CH:12]=1)[CH:8]([CH3:10])[CH3:9]>ClCCl.[O-2].[Cr+6].[O-2].[O-2]>[CH2:7]([C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:21])[CH2:18][CH:19]=[CH2:20])=[CH:15][CH:16]=1)[CH:8]([CH3:10])[CH3:9]To a stirred solution of pyridine (1.98 ml) in dichloromethane (15 ml) was added chromium(VI) oxide (1.23 g) at 0° C. After 30 minutes, 1-(4-isobutylphenyl)-3-buten-1-ol (525 mg) in dichloromethane (2 ml) was added and stirred for 20 minutes at ambient temperature. The reaction mixture was filtered through Florisil and washed with ether. The filtrate was concentrated in vacuo and chromatographed on silica gel (hexane:dichloromethane=1:1) to give 1-(4-isobutylphenyl)-3-buten-1-one (424 mg).
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