反应详情

A mixture of 4-chloro-2-methylbenzaldehyde (3.5 g, 22.6 mmol) and aniline (2.11 g, 22.6 mmol) in toluene (40 ml) was heated at reflux in a Dean-Stark apparatus for 1 hour. The mixture was cooled and evaporated in vacuo to leave an oily residue. The residue was redissolved in ether, washed with 5% sodium bicarbonate solution. The organic phase was separated, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to afford an oily residue which was purified by distillation via a Kugelrohr apparatus (oven temperature 160° C., 0.5 mm) to provide the title compound (4.0 g, 7.4 mmol, 77%) as a viscous oil; pmr(CDCl3) δ 2.5 (3H, s), 6.3~7.5 (7H, m), 7.95 (H, d), 8.6 (H, s).

1. temperaturewas heated
2. temperatureat reflux in a Dean-Stark apparatus for 1 hour
3. temperatureThe mixture was cooled
4. customevaporated in vacuo
5. customto leave an oily residue
6. washwashed with 5% sodium bicarbonate solution
7. customThe organic phase was separated
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationThe filtrate was concentrated in vacuo
11. customto afford an oily residue which
12. distillationwas purified by distillation via a Kugelrohr apparatus (oven temperature 160° C., 0.5 mm)