1-Phenethylamine, (-)- → HCID 7015460, compound

Participants

Reaction Steps

l-(-)-α-Methylbenzylamine (21.0 g) was added to a solution of racemic 3-phenoxymandelic acid (67.0 g) in isopropyl alcohol (700 ml) and the mixture kept for 24 hours at the ambient temperature. The solid precipitate was collected by filtration, (the filtrate kept -- see below) and recrystallized twice from isopropyl alcohol (200 ml) to yield the l-(-)-α-methylbenzylammonium salt of (S)-3-phenoxymandelic acid, m.p. 153° C. This was then shaken with a mixture of diethyl ether (150 ml) and 5N hydrochloric acid (25 ml), the ether layer separated, washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation of the ether under reduced pressure to yield a residue of solid (S)-3-phenoxymandelic acid, m.p. 110°-112° C., [α]D25 + 85° (C, 1.5, methanol).

Provenance & Evidence