Acetamide → Acetaminophen

HRID 342171

Reaction equation

HRID 342171 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)O.[C:9]([NH2:12])(=[O:11])[CH3:10]>O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W]>[C:9]([NH:12][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 178AcetamideHCID 785Hydroquinone

Product 1

HCID 1983Acetaminophen

Reagents, catalysts & solvents 1

HCID 45231312-Wolframophosphoric acidCatalyst

Procedure

An intimate mixture of hydroquinone (5.5 g), acetamide (3.5 g) and phosphotungstic acid (0.3 g) was placed in a well stoppered stainless steel tube from which air has been displaced with nitrogen. The tube was kept in a temperature controlled oven at 280°-300° C. for 1.5 hrs. The tube was then removed from the oven, cooled, opened, contents extracted with ethyl acetate, crystallized and products analyzed by gas chromatography. Pure standard substances were used for calibration. The products were also analyzed and identified by GC-mass spectroscopy techniques. The conversion of hydroquinone was 95% by wt. and selectivity to N-acetyl para aminophenol was 86%. Pure N-acetyl para aminophenol could be isolated from the products by column chromatography using alumina.

Workup

  1. customThe tube was then removed from the oven
  2. temperaturecooled
  3. extractioncontents extracted with ethyl acetate
  4. customcrystallized

Sources & evidence

ORD record
ord-0a6d23bd603b4001be9243f7118d11a0
Source dataset
uspto-grants-1999_01
Patent number
US05856575

Linked notes

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