Acetic Anhydride → 3-Hydroxyacetanilide

HRID 35418

Reaction equation

HRID 35418 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>O>[CH3:10][C:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=1)=[O:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 115683-Aminophenol

Product 1

HCID 121243-HydroxyacetanilideYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 66.0 g (0.60 mole) of 3-aminophenol in 180 mL of water was added dropwise 77.9 g (0.76 mole) of acetic anhydride. After complete addition, the reaction mixture was heated on a steam bath for 10 minutes, then cooled to 0° C. A precipitate formed and was collected by filtration. The filter cake was washed with cold water and dried in a desiccator for two hours to yield 81.0 g of 3-hydroxyacetanilide (mp 144°-146° C.).

Workup

  1. additionAfter complete addition
  2. temperaturethe reaction mixture was heated on a steam bath for 10 minutes
  3. customA precipitate formed
  4. filtrationwas collected by filtration
  5. washThe filter cake was washed with cold water
  6. customdried in a desiccator for two hours

Sources & evidence

ORD record
ord-942e1905c51f4c43895ec9e90acc6ad0
Source dataset
uspto-grants-1988_08
Patent number
US04766233

Linked notes

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