Acetic Acid → 1-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrile

Participants

Reaction Steps

A mixture of 33.9 g. (0.123 mole) of methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexanecarboxylate (prepared in Example 8) in 900 ml. of acetic acid and 450 ml. of 10% sulfuric acid is stirred mechanically on a steam bath for about 24 hours. The mixture is then allowed to cool and diluted with water. This mixture is extracted thoroughly with benzene. The organic layer is washed successively with water, sodium bicarbonate solution and brine and evaporated to dryness. The solid residue is recrystallized from ether to give 16.32 g. (75% yield) of 4-cyano-4-(4-fluorophenyl)cyclohexanone, having a melting point of 84° to 88°C.

Provenance & Evidence