Hydrochloric Acid → HCID 12692289, compound

HRID 365019Notes

Reaction equation

HRID 365019 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C@H:11]([OH:15])[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20]O>>[O:1]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C@H:11]([OH:15])[C:12]([O:14][CH3:20])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7015460HCID 7015460, compound

Product 1

HCID 12692289HCID 12692289, compound

Procedure

(S)-3-Phenoxymandelic acid (13.0 g) was added to a solution of dry hydrogen chloride (15.0 g) in methanol (100 ml) and the solution thus obtained kept at the ambient temperature for 24 hours after which period the volatile portion was evaporated yielding methyl (S)-3-phenoxymandelate as a residual oil. This was then added to liquid ammonia (20 ml) in a pressure vessel which was then sealed and temperature of the mixture allowed to rise to the ambient temperature over a period of 24 hours. The vessel was then opened and the excess of ammonia allowed to evaporate. The residual material was stirred with water and the solid collected by filtration, and recrystallised from benzene (70 ml) to yield impure(S)-3-phenoxymandelamide, m.p. 93° C. [α]D25 +25.4° (C, 2.0, methanol), (approximately 80% optically pure).

Workup

  1. customthe solution thus obtained
  2. customafter which period the volatile portion was evaporated

Sources & evidence

ORD record
ord-68c90fee2ac84492b138214a0288f23f
Source dataset
uspto-grants-1986_08
Patent number
US04607119

Reaction notes

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