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

HRID 614714Notes

Reaction equation

HRID 614714 reaction equation
C[C@H](N)C1C=CC=CC=1.[O:10]([C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[CH:20]([OH:24])[C:21]([OH:23])=[O:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(C)C>[O:10]([C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[C@H:20]([OH:24])[C:21]([OH:23])=[O:22])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 2760344HCID 2760344, compound

Product 1

HCID 7015460HCID 7015460, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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).

Workup

  1. filtrationThe solid precipitate was collected by filtration
  2. customrecrystallized twice from isopropyl alcohol (200 ml)

Sources & evidence

ORD record
ord-cc2c115aefec44d6ab78ede6cf5d5097
Source dataset
uspto-grants-1979_03
Patent number
US04146554

Reaction notes

Loading…