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

HRID 1074511Notes

Reaction equation

HRID 1074511 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 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).

Workup

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

Sources & evidence

ORD record
ord-fca3abcf4c3141f6a20b375b6a626ab4
Source dataset
uspto-grants-1983_07
Patent number
US04391983

Reaction notes

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