Acetanilide: Aniline Boiled with Glacial Acetic Acid

Acetanilide is aniline with an acetyl group on it, the starting point for p-nitroaniline and other dye intermediates. Yvon's method (US Dispensatory, 1907): boil aniline with glacial acetic acid under a reflux condenser for four hours, distil off the excess up to 260 °C, and crystallise the residue from water. Our batch is a quarter of his. Aniline poisons through the skin: gloves throughout. The picture: acetanilide crystals (Wikimedia Commons).