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

Participants

Reaction Steps

In a 1 l. flask under an atmosphere of dry nitrogen there was placed 26.4 g. of a 50% oil dispersion of sodium hydride together with 240 ml. of dry tetrahydrofuran. While this mixture was refluxed there was added thereto dropwise over a period of about 1 hour a mixture of 40.6 g. of methyl pivalate and 22.6 g. of acetonitrile in 40 ml. of dry tetrahydrofuran. When addition was complete, the mixture was refluxed overnight. The reaction mixture was worked up by evaporating part of the tetrahydrofuran in vacuo and dissolving the remaining solution in about 300 ml. of water. This aqueous mixture was acidified to about pH 4 using concentrated aqueous hydrochloric acid. The remainder of the tetrahydrofuran was then removed using a rotovapor. The solid which was formed was filtered and slurried with 150 ml. of hexane to remove mineral oil. The crystals were filtered and dried. The crystals had a melting point of about 57°-59° C. and were identified as pivalyl acetonitrile. Yield: 36.3 g. (83%).

Provenance & Evidence