Hydrochloric Acid → 1-(2-Fluorophenyl)-4-oxocyclohexane-1-carbonitrile

Participants

Reaction Steps

Methyl 5-cyano-5-(2-fluorophenyl)-2-oxocyclohexane-1-carboxylate (D19, 30.66 g, 0.11 mol) was stirred at reflux in c. HCl (500 ml) for 17 h, cooled, diluted with water (500 ml), and extracted with ethyl acetate. This organic portion was extracted with potassium carbonate solution, dried (Na2SO4) and evaporated to give 4-cyano-4-(2-fluorophenyl)cyclohexanone (9.58 g, 38%) as a yellow foam. The alkaline extract was re-acidified with c. HCl, and the product isolated by extraction with ethyl acetate, drying (Na2SO4) and evaporation. This gave the title compound (16.36 g, 62%) as a colourless gum.

Provenance & Evidence