Acetaminophen → Acetanilide, 4'-allyloxy-

HRID 1977441Notes

Reaction equation

HRID 1977441 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(C)=O>[CH3:2][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]

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 23103Acetanilide, 4'-allyloxy-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Acetamidophenol (383 g, 2.53 mole), allyl bromide (338 g, 2.79 mole), and anhydrous potassium carbonate (350 g, 2.53 mole) were added to acetone (2250 ml). Under intense stirring, the heterogeneous mixture was refluxed overnight. After cooling, the inorganic salts were filtered off and the filtrate concentrated under reduced pressure. The obtained solid was used for step 2 without purification.

Workup

  1. temperatureUnder intense stirring, the heterogeneous mixture was refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe inorganic salts were filtered off
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe obtained solid was used for step 2 without purification

Sources & evidence

ORD record
ord-9fb489667e744678804d929c5c8c0e89
Source dataset
uspto-grants-2001_05
Patent number
US06232430B1

Reaction notes

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