Phosphorus oxide (P4O10) → 1-(5,5-Dimethylcyclohex-1-en-1-yl)ethan-1-one

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Reaction Steps

Phosphorus pentoxide (33.1 g, 233 mmol) was added to a solution of 1-ethynyl-3,3-dimethylcyclohexanol (152 g, 1.00 mol) in MePh (800 ml). The slurry was heated to reflux, and stirred at this temp. for 90 min. The reaction mixture was allowed to cool to room temp., and then poured into ice/water (1:1, 500 ml). The product was extracted with Et2O (2×500 ml), and the combined organic extracts were washed with water (500 ml) and brine (100 ml), dried (Na2SO4) and concentrated under reduced pressure. Silica-gel FC (pentane/Et2O, 9:1, Rf=0.70) provided 13.8 g (9%) of 1-(5′,5′-dimethylcyclohex-1′-enyl)ethanone.

Provenance & Evidence