Acetaminophen → HCID 86737702, compound

HRID 1065053Notes

Reaction equation

HRID 1065053 reaction equation
C[C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.[C:12]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:14])[CH3:13].[C:23](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:23][C:16]1([NH:15][C:12](=[O:14])[CH3:13])[CH:21]=[CH:20][C:19]([O:22][CH2:7][C:6]([C:5]2[CH:4]=[CH:3][CH:2]=[CH:11][CH:10]=2)=[O:9])=[CH:18][CH2:17]1

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 692722-Bromo-4'-methylacetophenone

Product 1

HCID 86737702HCID 86737702, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Methylphenacyl chloride (XVI: X=Cl) (8.4 g, 0.05 mole), 4-acetamidophenol (XV: R=CH3) (7.6 g, 0.05 mole) and anhydrous potassium carbonate (8.3 g, 0.06 mole) were added to acetone (200 ml), and the mixture was heated under reflux for 12 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 32 to obtain 11.7 g of 4-methyl-α-(4-acetamidophenoxy)acetophenone (XVIII: R=CH3) as white crystals (yield, 82.7%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. additionThereafter, the reaction mixture was treated in the same manner as in Example 32
  4. customto obtain

Sources & evidence

ORD record
ord-66ddcc0958e44c4aa755364da272f739
Source dataset
uspto-grants-1982_05
Patent number
US04328166

Reaction notes

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