Ethanolamine → 1,2-Diphenyl-2-methoxy-1-(2-hydroxyethylimino)ethane

Participants

Reaction Conditions

Reaction Steps

Ethanolamine, 8.34 g (0.137 mole) and 4.52 g (0.020 mole) of 2-methoxy-1,2-diphenylethanone were mixed together and heated at 120° C. under a gentle stream of nitrogen for 2 hr. Mass spec analysis indicated none of the 2-methoxy-1,2-diphenylethanone remained. The mixture stood at ambient temperature for 16 hr, after which it was dissolved in 20 ml of methanol. The solution was poured into 100 ml of water. A yellow oil separated which became semisolid after 1 hr. The semisolid was extracted twice with 50 ml portions of methylene chloride. The extract was dried over magnesium sulfate, filtered, and concentrated to give 5.04 g of yellow oil (94%) which began to solidify on standing. Trituration with petroleum ether gave 2.19 g of off-white solid after filtration. The filtrate was concentrated to give an additional 2.25 g of yellow oil which was identical to the white solid and which crystallized on standing.

Provenance & Evidence