Acetaminophen → N-(4-Methoxyphenyl)Acetamide

HRID 1262730Notes

Reaction equation

HRID 1262730 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].[C:12](=O)([O-])[O-].[K+].[K+].P(OC)(OC)(OC)=O>>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1983AcetaminophenHCID 10541Trimethyl PhosphateHCID 11430Potassium Carbonate

Product 1

HCID 5827N-(4-Methoxyphenyl)AcetamideYield 281.1%

Conditions

Temperature
90 °C

Procedure

To a three-necked 100 ml flask equipped for reflux and fitted with a mechanical stirrer was added 10.0 g (0.066 mol) of p-acetamidophenol, 2.0 g (0.014 mol) of potassium carbonate, and 20 ml (0.17 mol) of trimethyl phosphate. The mixture was heated to 90° C. for three hours then allowed to stand overnight before quenching with 50 ml of water. Extraction into methylene chloride and removal of residual starting material via a base wash with 6% sodium hydroxide solution gave on concentration in vacuo 6.5 g (60%) of p-acetamidoanisole.

Workup

  1. customTo a three-necked 100 ml flask equipped
  2. temperaturefor reflux
  3. customfitted with a mechanical stirrer
  4. custombefore quenching with 50 ml of water
  5. extractionExtraction
  6. custominto methylene chloride and removal
  7. washwash with 6% sodium hydroxide solution

Sources & evidence

ORD record
ord-d56186de1b164a288180579de3360165
Source dataset
uspto-grants-1984_06
Patent number
US04453017

Reaction notes

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