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 recrystallised 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 5 N hydrochloric acid (25 ml), the ether layer separated, washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation and 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