N,N-Dimethylbenzylamine → 3-Ethoxy-4-hydroxybenzaldehyde;2-methylpropanoic acid

Participants

Reaction Steps

166 g (1 mol) of ethylvanillin and 160 g (1.33 mol) of N,N-dimethylbenzylamine are introduced into 800 ml of tert-butyl methyl ether in a stirred apparatus with the exclusion of moisture. 128 g (1.2 mol) of isobutyroyl chloride are added over the course of 1.5 h, during which the reaction temperature rises to about 38° C. The reaction mixture is stirred overnight at room temperature and then poured into about 1 l of water. The organic phase is separated off, washed with hydrochloric acid, 5% sodium hydroxide solution and water, dried and evaporated, giving a residue of 238 g of crude ethylvanillin isobutyrate, which is recrystallized from 240 ml of isopropanol. Yield 215 g of ethylvanillin isobutyrate; m.p. 57° C.

Provenance & Evidence