Acetaminophen → N-(4-Methoxyphenyl)Acetamide

HRID 1262711Notes

Reaction equation

HRID 1262711 reaction equation
S([O:5][CH3:6])(OC)=O.C(=O)([O-])[O-].[K+].[K+].[C:13]([NH:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1)(=[O:15])[CH3:14]>>[C:13]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:5][CH3:6])=[CH:19][CH:18]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 69223Dimethyl sulfite

Product 1

HCID 5827N-(4-Methoxyphenyl)AcetamideYield 73%

Conditions

Temperature
70 °C

Procedure

To a three-necked 100 ml flask equipped for reflux and fitted with a mechanical stirrer was added 10 ml (0.12 mol) of dimethyl sulfite, 2.0 g (0.014 mol) of potassium carbonate, and 5.0 g (0.033 mol) of p-acetamidophenol. The mixture was heated to 70° C. for six hours then quenched while hot with 50 ml of water. The solution was made basic with dilute caustic and the organic materials were extracted into methylene chloride. The extracts were concentrated in vacuo to give 2.0 g (73%) of p-acetamidoanisole (based on recovered starting material).

Workup

  1. customTo a three-necked 100 ml flask equipped
  2. temperaturefor reflux
  3. customfitted with a mechanical stirrer
  4. customthen quenched while hot with 50 ml of water
  5. additionwith dilute caustic
  6. extractionthe organic materials were extracted into methylene chloride
  7. concentrationThe extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-f2d791c25a1e4213b61f5237f83423d3
Source dataset
uspto-grants-1984_06
Patent number
US04453004

Reaction notes

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