p-Toluenesulfonic acid → Isobutyrophenone 2,4,6-Trimethylphenylimine

Participants

Reaction Conditions

Reaction Steps

2,4,6-Trimethylaniline (16.9 mL, 120 mmol, Aldrich) was mixed with isobutyrophenone (12.0 mL, 80 mmol, Acros) and p-TsOH (1.5 g, 8.0 mmol, Aldrich). The resulting mixture was heated for 10 h at 220° C. in a flask equipped with a Dean-Stark trap. Vacuum distillation afforded two fractions: 1. unreacted starting materials, 40–48° C./40 Pa; 2. product as a yellow oil, 98–108° C./13 Pa (6.2 g, 29.2%). 1H NMR (toluene-d8, 353 K) 7.28–6.78 (m, 4H); 6.62 (s, 2H); 2.96 (septet, 1H; J=6.7 Hz); 2.07 (s, 3H); 1.97 (s, 6H); 1.23 (d, 6H; J=6.7 Hz).

Provenance & Evidence