In a
2-l. beaker fitted with a strong, efficient, mechanical stirrer is placed a mixture of
106 g. (101 ml., 1 mole) of freshly distilled benzaldehyde and
117 g. (1 mole) of purified dry benzyl cyanide (Note
1), in
650 ml. of 95% ethanol (Note
2). To this mixture is added drop-wise, with stirring, a solution of
7 g. of sodium ethoxide in 50 ml. of absolute ethanol (Note
3). When 40–50 ml. has been added, the mixture becomes warm, turns cloudy, and solidifies. Mechanical stirring is continued as long as possible, and then the mixture is stirred by hand with a thick
stirring rod in order to break up the lumps that form. The mixture is cooled in an
ice bath (Note
4), and the product is separated by filtration. The filtrate is removed and may be saved (Note
5). The white mass is washed first with 200 ml. of distilled water, then with
50 ml. of 95% ethanol to remove unchanged reagents. The nitrile is dried at 25° and melts at
86–88°. The yield is
178–199 g. (
87–97%) of product sufficiently pure for most purposes. Recrystallization from
700 ml. of 95% ethanol gives
170–187 g. (
83–91%) of a pure, white product melting at
88° (Note
6).