N-Capronitrile

Place 29 g. of n-caproamide (Section 111,109) into a 200 ml. distilling flask, and assemble the apparatus shown in Fig. Ill, 28, 1. Remove the trap momentarily and introduce 45 g. (27-5 ml.) of redistilled thionyl chloride no apparent reaction takes place in the cold. Warm the mixture on a water bath or by means of a small flame for 1 hour. Arrange the apparatus for distillation and distil oflF the excess of thionyl chloride (t.c., until the temperature reaches about 90°) and allow to cool. When cold, transfer the residue to a 100 ml. distilling flask (1). Distil from an air bath (Fig. II, 5, 3) the n-capronitrile passes over at 161-163° (2). The yield is 21 g. 

The n-capronitrile is sometimes slightly turbid the turbidity is readily removed by shaldng with a little anhydrous calcium sulphate. 

For practice, the student should carry out both alkaUne (compare Section 111,83) and acid hydrolysis of acetonitrile, n-valeronitrile (n-butyl cyanide) and n-capronitrile (n-amyl cyanide). 

Rinehart also used sandpapered zinc foil for the reaction of n-capronitrile with iec-butyl a-bromopropionate to produce rec-butyl a-n-caproylpropionate, but added a catalytic amount of cupric bromide. The ratio of zinc bromo ester nitrile was... 

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