Acetaminophen → 4'-Allyloxyacetanilide
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureUnder intense stirring, the heterogeneous mixture was refluxed overnight
- temperatureAfter cooling
- filtrationthe inorganic salts were filtered off
- concentrationthe filtrate concentrated under reduced pressure
- 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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