In a
1-l. round-bottomed flask, bearing an
efficient reflux condenser (Note
1), are placed
286 g. (2 moles) of 2-ethylhexanamide (Note
2),
300 ml. of dry benzene (Note
3), and
357 g. (218 ml., 3 moles) of thionyl chloride (Note
4). The flask is placed in a
water bath, which is heated quickly to 75–80° and maintained at that temperature for 4.5 hours (Note
5). The reaction mixture is transferred to a
1.5-l. beaker and cooled in an
ice bath. A mixture of 100 g. of crushed ice and 100 ml. of water is added to decompose the excess
thionyl chloride. Cold
50% potassium hydroxide solution is added in small portions, with stirring, until the mixture is alkaline to litmus (Note
6). The mixture is transferred to a
separatory funnel, and the layers are separated. The aqueous portion is extracted with
100 ml. of benzene. The
benzene solutions are combined and washed once with
150 ml. of 1% sodium carbonate solution and twice with 150-ml. portions of water (Note
7). The mixture is distilled from a
modified Claisen flask, the bulk of the solvent being removed at atmospheric pressure. The yield of nitrile is
215–236 g. (
86–94%); b.p.
118–120°/100 mm. (Note
8), (Note
9), and (Note
10).