Acetic Anhydride → Acetamide, N-(4-hydroxy-2,5-dimethylphenyl)-

HRID 1822898

Reaction equation

HRID 1822898 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>O>[OH:9][C:5]1[C:4]([CH3:10])=[CH:3][C:2]([NH:1][C:11](=[O:13])[CH3:12])=[C:7]([CH3:8])[CH:6]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 765444-Amino-2,5-dimethylphenol

Product 1

HCID 155307Acetamide, N-(4-hydroxy-2,5-dimethylphenyl)-Yield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 4-amino-2,5-dimethyl-phenol (6.85 g, 50 mmol) in 30 mL of water was added acetic anhydride (5.67 mL, 60 mmol). The mixture was vigorously stirred at 70° C. for 20 min and then cooled down to room temperature. The solid was collected by filtration and washed with water to give N-(4-hydroxy-2,5-dimethyl-phenyl)-acetamide as gray solid (8.1 g, 90%).

Workup

  1. temperaturecooled down to room temperature
  2. filtrationThe solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-319565c3bd714555a2d8cd31a5c25312
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Linked notes

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