Acetaminophen → Acetanilide, 4'-allyloxy-

HRID 361698Notes

Reaction equation

HRID 361698 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][CH:13]=[CH2:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 23103Acetanilide, 4'-allyloxy-

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Commercially available 4-acetamido phenol (1 molar equivalent), allyl bromide (1 molar equivalent) and potassium carbonate (1 molar equivalent) in butan-2-one were heated at reflux for 18 hours with stirring. The mixture was cooled, filtered and the solid residue washed with ether. The combined filtrates were evaporated and the solid residue was further purified by crystallisation from ethyl acetate-hexane to give 4-acetamido-1-allyloxy benzene as a colourless solid, m.p. 85°-86° C.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe solid residue washed with ether
  5. customThe combined filtrates were evaporated
  6. customthe solid residue was further purified by crystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-00d330a9d291460891b62d2b6f79ce4c
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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