p-Toluenesulfonic acid monohydrate → 4-Benzylcyclohexanone

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Reaction Steps

To a solution in toluene (44.0 mL) of the compound (1.28 g) obtained in step (1) above, p-toluenesulfonic acid monohydrate (84.0 mg) was added and thereafter the mixture was refluxed for 3 hours with a Dean-Stark apparatus. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-50:50). A suspension of the resulting purified product (935 mg) and 20% palladium hydroxide/carbon (93.5 mg) in methanol (11.3 mL) was stirred at room temperature for 5 hours in a hydrogen atmosphere. The reaction mixture was filtered through Celite (registered trademark). The filtrate was concentrated under reduced pressure. To a solution of the resulting residue (938 mg) in tetrahydrofuran (34.3 mL), 1 mol/L hydrochloric acid (9.30 mL) was added at 0° C. and the mixture was stirred at room temperature for 14.5 hours. After concentrating the stirred mixture under reduced pressure, three extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine. After passage through a phase separator, the washed organic layers were concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-50:50) to give the titled compound as a colorless oil (225 mg).

Provenance & Evidence