2-(o-Tolyl)acetonitrile → Ethyl 5-cyano-4-oxo-5-(2-methylphenyl)pentanoate

Participants

Reaction Steps

Diethyl succinate (510 g.) and 2-methylbenzyl cyanide [prepared according to the method of Meisenheimer et al, Ann. 468, 217 (1929); 155 g.] were added to a solution of sodium (42 g.) in dry methanol (585 ml.) at ambient temperature. The mixture was heated under reflux, with stirring, for 16 hours and excess methanol was then removed by distillation under reduced pressure. The residue was dissolved in a mixture of toluene (500 ml.) and water (2000 ml.). The aqueous layer was separated, acidified with concentrated sulphuric acid (50 ml.) and extracted with diethyl ether (3 × 800 ml.). The ethereal extract was washed with water, dried over sodium sulphate and evaporated to dryness to give ethyl 5-cyano-4-oxo-5-(2-methylphenyl)pentanoate (305 g.) in the form of a dark coloured oil.

Provenance & Evidence