Acetic Anhydride → 3',5'-Dichloro-4'-hydroxyacetanilide

HRID 361703Notes

Reaction equation

HRID 361703 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([OH:16])=[C:11]([Cl:17])[CH:10]=1>O>[C:1]([NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([OH:16])=[C:11]([Cl:17])[CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 800374-Amino-2,6-dichlorophenol

Product 1

HCID 100821803',5'-Dichloro-4'-hydroxyacetanilide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic anhydride (7.lml) was added to a suspension of 4-amino-2,6-dichlorophenol (5.34 g) in-water (50 ml). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to ambient temperature and the crude product was collected by filtration, washed with water and then washed with pentane to give 4-acetamido-2,6-dichlorophenol as a solid (5.6 g), m.p. 151°-152°; NMR ([CD3 ]2SO): 2.0(3H,s), 7.58(2H,s) and 9.92(2H,br s); m/z 220 (M+H).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationthe crude product was collected by filtration
  3. washwashed with water
  4. washwashed with pentane

Sources & evidence

ORD record
ord-4b4161dbb4134dd88352e549d49e33ae
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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