Water → Benzylidene-p-(1-methyl-heptyloxy)aniline

Participants

Reaction Steps

Benzylidene-p-hydroxyaniline as a known substance (m.p.: 185° C.) (140 g) was dissolved in ethanol (700 ml) containing KOH (43 g), followed by dropwise adding S(+)-2-octyl p-toluenesulfonate (218 g) at 70° C., heating the mixture under reflux for 20 hours, adding a 5% aqueous solution of NaHCO3 (50 ml), water (200 ml) and toluene (800 ml), separating the toluene layer, washing with a 2N aqueous solution of NaOH, distilling off toluene and recrystallizing from ethanol to obtain optically active benzylidene-p-(1-methyl-heptyloxy)aniline (m.p. 47.3° C.)(105 g).

Provenance & Evidence