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

HRID 724752Notes

Reaction equation

HRID 724752 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([OH:10])=[C:5]([Cl:11])[CH:4]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>O>[Cl:9][C:7]1[CH:8]=[C:3]([CH:4]=[C:5]([Cl:11])[C:6]=1[OH:10])[NH:2][C:12](=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 162059Phenol, 4-amino-2,6-dichloro-, hydrochloride (1:1)

Product 1

HCID 100821803',5'-Dichloro-4'-hydroxyacetanilideYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Into a 500 ml round bottom flask (fitted with a magnetic stirrer), water (200 ml) was mixed with 4-amino-2,6-dichlorophenol hydrochloride (20 g) until the solid was completely dissolved. The resulting solution was warmed to 70° C., and to it was added acetic anhydride (11 g) and the resulting solution was stirred for 1 hour. Upon cooling, crystals of 3',5'-dichloro-4'-hydroxyacetanilide were formed (19.6 g, 95% yield).

Workup

  1. dissolutionwas completely dissolved
  2. temperatureUpon cooling

Sources & evidence

ORD record
ord-b07a513a7d604496b867697bd9c8770f
Source dataset
uspto-grants-1998_01
Patent number
US05705357

Reaction notes

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