3,4-Dimethylbenzaldehyde → HCID 72490709, compound

Participants

Reaction Steps

To a solution of t-butyl carbazate (5.06 g, 38.3 mmol) in ethyl acetate (15 mL) was added with stirring 3,4-dimethylbenzaldehyde (5.20 mL, 5.26 g, 39.2 mmol). Crystallization occurred and the resulting slurry was stirred at rt for 45 min. Hexanes (70 mL) was added and the slurry was cooled to 0° C. The slurry was stirred at 0° C. for 60 min, then filtered and rinsed with cold hexanes (20 mL), and dried in vacuo at 40° C. to afford the title compound as a solid (8.76 g, 92.1%): mp 167.7-168.6° C. 1H NMR (DMSO-d6) δ 10.82 (s, 1H), 7.92 (s, 1H), 7.36 (s, 1H), 7.28 (d, 2H, J=3 Hz), 7.14 (d, 2H, J=3 Hz), 2.206 (s, 3H), 2.20 (s, 3H) 1.44 (s, 9H); 13C NMR (DMSO-d6) δ 153.0, 144.1, 138.5, 137.3, 132.9, 130.5, 128.1, 124.8, 79.9, 28.8, 19.99, 19.97; IR (KBr mull) 3361, 3009, 2981, 2981, 1513, 1495 cm−1. A portion was further purified by recrystallization from ethyl acetate for analysis. Anal. Calcd. for C14H20N2O2: C, 67.71; H, 8.12; N, 11.28. Found: C, 67.51; H, 8.07; N, 11.22.

Provenance & Evidence