[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][O:13][C:14]1[C:15]([CH3:22])=[C:16]([CH2:20][OH:21])[CH:17]=[CH:18][CH:19]=1.CCOCC.CCCCCC>ClCCl.C(OCC)C>[CH3:12][O:13][C:14]1[C:15]([CH3:22])=[C:16]([CH:17]=[CH:18][CH:19]=1)[CH:20]=[O:21]A stirred suspension of pyridinium chlorochromate (19.2 g; 89.2 mmol) in dichloromethane at ambient temperature was treated with a solution of (3-methoxy-2-methylphenyl)methanol (9.05 g; 59.47 mmol) in dichloromethane. The reaction solution immediately turned a greenish-brown color. The reaction was stirred for 3.5 hr, diluted 50% with diethyl ether and decanted. The brown gummy residue was triturated twice more with diethyl ether (40 mL) and the ether extracts were combined and evaporated to yield a yellow oil. The oil was passed through a column of silica gel with an ether/hexane mixture to yield the title product, 8.74 g; 97% yield.
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