Acetic Acid → Methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate

Participants

Reaction Steps

4-cyano-4-phenylheptanedioic acid dimethyl ester (14.45 g, 0.05 mole) was dissolved in dry tetrahydrofuran (350 ml). Sodium tert-butylate (9.6 g, 0.1 mole) was then added in portions. During this addition the reaction mixture turned an orange colour. The reaction mixture was then boiled under reflux for 5 hours. During the boiling a beige-coloured pasty suspension was formed. The reaction mixture was cooled to room temperature overnight. 2.5N acetic acid (170 ml) was slowly added dropwise to the reaction mixture while cooling with ice. Toluene (100 ml) was then added to the reaction mixture. The organic phase was separated and washed with saturated sodium hydrogen carbonate solution (3×70 ml), water (3×50 ml) and sodium chloride solution (1×70 ml). After drying over Na2SO4, the solvent was distilled off on a rotary evaporator and the residue was recrystallised from methanol. The desired product was obtained in a yield of 10.7 g (83%) as a yellow solid with a melting point of 75°-80° C.

Provenance & Evidence