Ammonia → 4-Hydroxy-4-phenylbutanamide

HRID 429172Notes

Reaction equation

HRID 429172 reaction equation
[C:1]1([CH:7]2[O:12][C:10](=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:13]>>[OH:12][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH2:9][C:10]([NH2:13])=[O:11]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 13884gamma-Phenyl-gamma-butyrolactone

Product 1

HCID 114239224-Hydroxy-4-phenylbutanamideYield 75%

Procedure

A mixture of γ-phenyl-γ-butyrolactone (10.30 g, 63.5 mmol) and an excess of ammonia was stirred under nitrogen and a dry ice trap for 8 hours. The dry ice trap was removed and after evaporation of the ammonia 11.27 g of a tan solid remained. Recrystallization of the solid from ethyl acetate-hexane gave 4-hydroxy4-phenyl-butyramide (8.56 g, 75%) as a white solid, mp 85-87° C.

Workup

  1. customThe dry ice trap was removed
  2. customafter evaporation of the ammonia 11.27 g of a tan solid
  3. customRecrystallization of the solid from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a4ea1a492f1f4bbc9729dcf30c88c50c
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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