Acetonitrile → 4-Chlorobenzoylacetonitrile

Participants

Reaction Steps

A 50% oil dispersion of NaH (24 grams) was placed in a 2 l. 3-necked flask and covered with 250 ml. THF. After heating to reflux, a solution composed of 55 ml. THF, ethyl-4-chlorobenzoate (57 grams), and acetonitrile (20.5 grams) was added in dropwise fashion. The reaction mixture started to solidify after the reactants were added so an additional 200 ml. of THF was added. The mixture was then heated to reflux for 21/2 hours, cooled to room temperature, treated with 1 l. ether, and allowed to stand for 72 hours.

Provenance & Evidence