4-(2-Oxazolyl)phenyl acetate → 4-(Oxazol-2-yl)phenol

HRID 16473

Reaction equation

HRID 16473 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH:13]=[CH:14][N:15]=2)=[CH:7][CH:6]=1)(=O)C>CO>[O:12]1[CH:13]=[CH:14][N:15]=[C:11]1[C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 684903404-(2-Oxazolyl)phenyl acetate

Product 1

HCID 1356214594-(Oxazol-2-yl)phenolYield 789.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2-oxazolyl)phenyl acetate (44.7 g, 22 mmol) in methanol (500 ml) was added an aqueous solution of potassium carbonate KOH (176 g in 800 mL, 5.8 eq.). The reaction was stirred at ambient temperature for 1 hour under nitrogen. Methanol was removed under reduced pressure and the residue was treated with concentrated hydrochloric acid to give a slurry with a pH of 6. The precipitated solid was isolated by filtration and dried to give 35 g. Recrystallization from methanol gave 4-(2-oxazolyl)phenol (28 g, 79% th.; 63% pract); 1H NMR (DMSO) δ 10.05 (s, 1H), 8.10 (s, 1H), 7.75 (d, 2H), 7.20 (s, 1H), 6.85 (d, 2H) ppm.

Workup

  1. customMethanol was removed under reduced pressure
  2. additionthe residue was treated with concentrated hydrochloric acid
  3. customto give a slurry with a pH of 6
  4. customThe precipitated solid was isolated by filtration
  5. customdried
  6. customto give 35 g
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-b6d33b8822df4903a49d1840e98dd856
Source dataset
uspto-grants-2010_06
Patent number
US07737145B2

Linked notes

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