In a
3-l. three-necked flask, equipped with a
Hershberg stirrer, a
reflux condenser, and a
dropping funnel, are placed
175 g. (3.6 moles) of sodium cyanide and 125 ml. of distilled water (Note
1). The mixture is stirred until the
sodium cyanide is dissolved, and then, while vigorous stirring is continued,
535 g. (360 ml., 3.5 moles) of β-ethoxyethyl bromide (p. 370) in
260 ml. of 95% ethanol is added over a period of 15 minutes. The
separatory funnel is replaced by a 360°
thermometer, and the mixture is stirred and gently refluxed for 10 hours.
The mixture is then fractionally distilled until the temperature reaches 140°. The first fraction boiling at 75–95° consists mostly of
ethanol and water, and is discarded. The fraction boiling between 95° and 140° contains water and
25–30 g. of
β-ethoxypropionitrile. This is extracted twice with
50-ml. portions of benzene, and the
benzene extracts are added to the cooled residue in the distilling flask. The mixture is filtered (Note
2), the solid material is washed with
75 ml. of benzene, which is added to the filtrate, and the whole is distilled. The fraction boiling at
169–174° is collected; it weighs
178–200 g. (
52–58%).