Acetic Acid → Acetaminophen

HRID 1248476Notes

Reaction equation

HRID 1248476 reaction equation
[CH3:1][C:2]([NH:10]O)=[C:3]1[CH:9]=CC(=O)C=C1.[C:12]([OH:15])(=O)[CH3:13].S([O-])([O-])(=O)=O.[Mg+2].[CH2:22]([OH:24])[CH3:23]>>[C:22]([NH:10][C:2]1[CH:1]=[CH:13][C:12]([OH:15])=[CH:9][CH:3]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 178465686HCID 178465686, compound

Product 1

HCID 1983AcetaminophenYield 66.7%

Procedure

A mixture of 3.0 g of Amberlyst 15, (a sulfonic acid ion-exchange resin made by Rohm & Haas), 3.0 g (22.0 mmol) of 4-hydroxyacetophenone oxime, and 50 mL of acetic acid was heated at reflux under nitrogen for 2 h. The ion exchange resin was then removed and the acetic acid was distilled in vacuo to afford an orange residue. The residue was dissolved in ethanol and treated with activated carbon and anhydrous magnesium sulfate. Removal of the ethanol using a rotary evaporator produced 2.9 of a yellow oil, which upon drying afforded 2.0 g (66.7%) of N-acetyl-para-aminophenol.

Workup

  1. additionA mixture of 3.0 g of Amberlyst 15
  2. temperaturewas heated
  3. temperatureat reflux under nitrogen for 2 h
  4. customThe ion exchange resin was then removed
  5. distillationthe acetic acid was distilled in vacuo
  6. customto afford an orange residue
  7. customRemoval of the ethanol using
  8. customa rotary evaporator
  9. customproduced 2.9 of a yellow oil, which
  10. customupon drying

Sources & evidence

ORD record
ord-46fe6dfe4f354a47ae160105988cd4e6
Source dataset
uspto-grants-1985_06
Patent number
US04524217

Reaction notes

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