Benzyl Alcohol → 3-Benzyloxy-2-cyclohexen-1-one

Participants

Reaction Steps

To a round bottomed flask equipped with magnetic stirrer and Dean-Stark apparatus was added 1,3-cyclohexanedione (60.0 g, 535 mmol), toluene (450 ml), p-toluenesulfonic acid monohydrate (1.35 g, 5.20 mmol) and benzyl alcohol (52.6 g, 487 mmol). The resulting solution was heated to reflux temperature for 12 hr. The reaction mixture was cooled to room temperature and then washed with saturated aqueous sodium carbonate solution (2×100 ml). The organic layer was then washed with brine (100 ml), dried over magnesium sulfate, filtered and concentrated in vacuo, affording a brown oil (94.9 g) which crystallised upon standing for 17 hr. The crude crystalline material was slurried in isopropyl ether (20 ml). The mixture was filtered and the crystalline material was washed with ice cold isopropyl ether (3×30 ml), then with cold petroleum ether (2×20 ml). The resulting peach coloured crystalline solid was dried overnight under reduced pressure, furnishing the desired product (74.4 g, 76%). m/z (ES+) 203 (M+H+).

Provenance & Evidence