Acetic Anhydride → 4-Acetylamino-2-chlorophenol

HRID 361701Notes

Reaction equation

HRID 361701 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10](OC(=O)C)(=[O:12])[CH3:11]>O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:10](=[O:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[OH:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 775784-Amino-2-chlorophenol

Product 1

HCID 775794-Acetylamino-2-chlorophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture was heated at reflux for 6 hours, cooled to ambient temperature and filtered. The filtrate was evaporated, and the residue treated with ether to give crude 2-chloro-4-aminophenol (10 g). The crude 2-chloro-4-aminophenol (3.5 g) was added to a mixture of water (50 ml) and acetic anhydride (5.7 ml). The reaction mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to ambient temperature and the supernatant was decanted away from an oil which gave a solid on standing. The solid was purified by flash column chromatography on silica gel (Merck Art. No 9385) using a 1:2(v/v) mixture of ethyl acetate and pentane as eluent to give 2-chloro-4-acetamidophenol as an oil (1.7 g); NMR: ([CD3 ]2SO): 2.0(3H,s), 6.85(1H,d), 7.2(1H,m), 7.68(1H,m) and 9.8(2H,m).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe supernatant was decanted away from an oil which
  3. customgave a solid
  4. customThe solid was purified by flash column chromatography on silica gel (Merck Art
  5. additionmixture of ethyl acetate and pentane as eluent

Sources & evidence

ORD record
ord-a72e129dc4cd488180b72ebda6e766a2
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

Loading…