Water → N-(4-hydroxy-2-(trifluoromethyl)phenyl)acetamide

HRID 133740Notes

Reaction equation

HRID 133740 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[C:13](OC(=O)C)(=[O:15])[CH3:14].O>C(O)(=O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:13](=[O:15])[CH3:14])=[C:3]([C:9]([F:10])([F:11])[F:12])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 146928342-Amino-5-hydroxybenzotrifluoride

Product 1

HCID 22890936N-(4-hydroxy-2-(trifluoromethyl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Amino-3-trifluoromethylphenol (0.212 g; 1.2 mmol) was dissolved in 10 ml of glacial acetic acid under nitrogen atmosphere and acetic anhydride (0.3 ml; 3.0 mmol) was added followed with stirring for an hour at room temperature. Water (0.5 ml) was added into the reaction mixture and then evaporated to dryness. Toluene (50 ml) was added and the evaporation was repeated to give a quantitative yield of pure N-(4-Hydroxy-2-trifluoromethylphenyl)acetamide. 1H NMR (400 MHz, DMSO-d6): 1.99 (3H, s), 7.01 (1H, dd, J=8.6 Hz, J=2.6 Hz), 7.02 (1H, d, J=2.5 Hz), 7.19 (1H, d, J=8.4 Hz), 9.33 (1H, s), 10.08 (1H, br s).

Workup

  1. customevaporated to dryness
  2. additionToluene (50 ml) was added
  3. customthe evaporation

Sources & evidence

ORD record
ord-ab77e9a92b82499cb82efbce4d6f06bb
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

Loading…