3-Aminophenol → 3-Hydroxyacetanilide

HRID 1460902Notes

Reaction equation

HRID 1460902 reaction equation
[CH3:1][C:2](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:3].[NH2:25][C:26]1[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1>O>[C:2]([NH:25][C:26]1[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1)(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Product 1

HCID 121243-HydroxyacetanilideYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic anhhydride (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-e8fe6d4de04d4d80bb48f57764ff7fbc
Source dataset
uspto-grants-1991_12
Patent number
US05073173

Reaction notes

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