Acetic Anhydride → 3-Hydroxyacetanilide

HRID 2081350Notes

Reaction equation

HRID 2081350 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1>O>[C:1]([NH:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 115683-Aminophenol

Product 1

HCID 121243-HydroxyacetanilideYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic anhydride (21.2 ml, 220 mmol) was slowly added to a suspension of m-aminophenol (24.0 g, 220 mmol) in 60% of crushed ice and 60 ml of cold water. The reaction mixture was vigorously stirred for 30 minutes. The white precipitate was filtered, washed with cold water, and air-dried to give 30.5 g (92%) of pure 3-acetamidophenol, m.p. 147-149° C.

Workup

  1. filtrationThe white precipitate was filtered
  2. washwashed with cold water
  3. customair-dried

Sources & evidence

ORD record
ord-ec304dbd0bdb4d809a97f54021d39963
Source dataset
uspto-grants-1993_02
Patent number
US05183941

Reaction notes

Loading…