In a
3-l. round-bottomed flask, fitted with a
reflux condenser, is placed
650 cc. of absolute alcohol (Note
1), and to it
46 g. (2 gram atoms) of sodium is added as rapidly as possible without loss of material through the condenser. If the
sodium does not entirely dissolve, heat is applied. To the hot
sodium ethoxide solution
312 g. (2.1 moles) of ethyl oxalate (Org. Syn. Coll. Vol. I, 1941, 261) is added as rapidly as possible. Then, immediately,
234 g. (2 moles) of benzyl cyanide (Org. Syn. Coll. Vol. I, 1941, 107) is added, and the reaction mixture is allowed to stand overnight. The solution is transferred to a
3-l. beaker and treated with 250–300 cc. of water (Note
2). It is then warmed to 35° and made strongly acid to litmus with concentrated
hydrochloric acid. Mechanical stirring is used during the acidification. On cooling to ordinary temperatures the ester crystallizes. The yield is
360–385 g. of lemon-yellow crystals melting at
126–128°. On recrystallization from
60 per cent alcohol, the ester melts at
130°. The final yield is
300–325 g. (
69–75 per cent of the theoretical amount).