Ethanol → alpha-(Aminomethyl)-4-methoxybenzyl alcohol

Participants

Reaction Steps

2-Amino-1-(4-methoxyphenyl)ethanol was prepared according to the procedure of Evans et al., J. Org. Chem., 39, 914 (1974) by cyanosilylation of 4-methoxybenzaldehyde followed by lithium aluminum hydride reduction. The crude aminoalcohol (36.9 g) was dissolved in 150 mL of hot ethanol on a steam bath. To this mixture was slowly added 12.83 g of fumaric acid. The precipitated salt was filtered and washed with additional ethanol. Recrystallization from methanol provided greater than 99% pure 2:1 amine:fumarate salt.

Provenance & Evidence