N,N-Dimethylaniline → HCID 14838650, compound

Participants

Reaction Steps

A solution of methyl 2-allyloxy-4-chlorobenzoate (3f) (50.6 g, 0.22 mol) in 100 ml of N,N-dimethylaniline was heated under argon in an oil bath at 190°-205° C. for 20 hours. The solvent was removed by distillation and the residue purified by column chromatography (silica gel, CH2Cl2 /hexane) to give 4f (36.0 g, 71.1% yield) as a very light oil. IR (nujol) 1665 (C=0) cm-1. NMR (CDCl3) δ 11.23 (s, 1H, OH), 7.47 (d, 1H, J=9 Hz, aromatic proton meta to Cl), 6.77 (d, 1H, aromatic proton alpha to Cl), 6.17-4.77 (m, 3H, olefinic protons), 3.87 (s, 3H, CH3) and 3.50 (m, 2H, CH2).

Provenance & Evidence