Ethyl isovalerate → HCID 13374430, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.99 g (0.13 g. atm) of sodium in 50 ml of absolute ethanol, heated to 60° C., was added 11.81 g (0.09 m) of 3-methyl-benzyl cyanide followed by the slow addition, over a period of 20 minutes of 31.27 g (0.24 m) of ethyl isovalerate. The reaction mixture was heated under reflux overnight (18 hrs.). During this period the color of the solution turned from yellow to dark orange. After approximately 70 ml of solvent and excess of ethyl valerate was removed by distillation, 75 ml of toluene was added and additional 30 ml of the solvent was removed by heating the mixture to 112° C. The reaction mixture was cooled, diluted with 100 ml of toluene and was washed twice with water. The aqueous extracts were combined and acidified with 6N hydrochloric acid. The product was extracted in 300 ml of methylene chloride. The organic extract was washed with water, dried over magnesium sulfate and was concentrated under vacuum to afford 18.56 g of orange colored oil. Crystallization from ethyl acetate hexane solution afforded 14.0 g. of a white solid. m.p. 46.5°-50° C.

Provenance & Evidence