2-Chloroaniline → Propanamide, N-(2-chlorophenyl)-2,2-dimethyl-

Participants

Reaction Steps

To a solution of 2-chloroaniline 46 (200 mL, 1.9 mol) in MTBE (950 mL) in an ice-water bath was added 25 wt % NaOH (480 g, 3 mol). Trimethylacetyl chloride (248.5 mL, 2.02 mol) was then added dropwise and the reaction was stirred overnight at rt. The organic layer was separated, washed with brine (1.0 L) and water (1.0 L), dried over sodium sulfate, and concentrated in vacuo to give 47 (390 g, 97%) as a white solid.

Provenance & Evidence