Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-(4-Hydroxymethylphenyl)cyclohexanone

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Reaction Steps

To a solution of tert-butyl-[4-(1,4-dioxa-spiro[4.5]dec-8-yl)benzyloxy]dimethylsilane (12.1 g, 33.3 mmol) in acetone (12 ml) and water (1.2 ml) was added pyridinium p-toluenesulfonate (2.51 g, 9.99 mmol) at room temperature. The mixture was refluxed for 3 hours. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=60/40) to afford 4-(4-hydroxymethylphenyl)cyclohexanone as a colorless solid (4.21 g, 20.6 mmol, 62%).

Provenance & Evidence