Acetic Acid → 4-Oxo-1-phenylcyclohexanenitrile

Participants

Reaction Conditions

Reaction Steps

5-cyano-2-oxo-5-phenylcyclohexanecarboxylic acid methyl ester (7.71 g, 0.03 mole) was dissolved in 10 percent H2SO4 and conc. acetic acid (240 ml). The reaction mixture was stirred for 24 hours at 100° C. The course of the reaction was followed by thin layer chromatography. The reaction mixture was worked up by dilution with water (400 ml) while cooling in ice and extracted with ethyl acetate (3×100 ml). The organic phase was then thoroughly washed with water (6×100 ml), saturated sodium hydrogen carbonate solution (10×100 ml) and saturated sodium chloride solution (1×100 ml). After drying the organic phase over Na2SO4, the solvent was distilled off on a rotary evaporator. The desired product was obtained in a yield of 5.46 g (92%) with a melting point of 106°-107° C.

Provenance & Evidence