p-Toluidine → 4-Methylacetanilide

Participants

Reaction Steps

Into three neck round bottom flask (5 L) equipped with a mechanical stirrer, a condenser, and an addition funnel, were added p-toluidine (995 g, 9.3 mol) and hexanes (1.6 L). Acetic anhydride (960 mL, 10.2 mol) was added dropwise for 2 h enough to reflux, then refluxed for 1 h and cooled to room temperature to give a brown solid. This was collected by suction filtration, transferred into a beaker, and washed with water (2 L) for 30 min. The filtration and washing procedures were repeated. The wet white crystals were air dried for 7 days to provide N-(4-methylphenyl)acetamide (1,343 g, 97% yield). Melting point: 150-152° C. (lit. 153° C., Merck index. 11, 67;).

Provenance & Evidence