In a
1-l. round-bottomed flask equipped with a
reflux condenser are placed
157.5 g. (1 mole) of p-chloronitrobenzene,
160 g. (1 mole) of potassium xanthate (Note
1), and
450 ml. of 95% ethanol. This reaction mixture is heated under reflux on a
steam bath for 48 hours. The crystalline product, which deposits from solution during the course of the reaction, is collected by filtration, crushed into small particles in a
mortar, and washed twice with hot
ethanol and once with hot water. The yield of
p-nitrophenyl sulfide melting at
158–160° is
105–113 g. (
76–82%). This product is pure enough for most purposes. Recrystallization from
glacial acetic acid (15 ml. per gram) raises the melting point to
160–161°.