Acetonitrile → Pentanenitrile, 4,4-dimethyl-3-oxo-

Participants

Reaction Conditions

Reaction Steps

55 grams of sodium hydride (as an 80 weight % suspension in white oil) were suspended in 500 ml of dry toluene, 106 grams (0.914 mole) of methyl pivalate added and the mixture heated to 85° C. Then under vigorous stirring there was dropped in 77 grams (1.87 moles) of acetonitrile within 4 hours. Stirring was continued subsequently at 85° C. until the end of the development of hydrogen. The thickly liquid reaction mass was cooled to room temperature, treated with 700 ml of water, stirred vigorously for 30 minutes and the two phases separated in a separatory funnel. The aqueous phase was acidified with 31 weight % of hydrochloric acid at a pH 1-2 and 0° C. The precipitated pivaloylacetonitrile was filtered off with suction, washed until neutral with ice water and dried to constant weight at 25 Torr and 40° C. There were obtained 106 grams (93% of theory) of analytically pure pivaloylacetonitrile having a melting point of 65°-68° C.

Provenance & Evidence