Methyl 4-(1,3-oxazol-5-yl)benzoate → 4-(1,3-Oxazol-5-yl)benzoic Acid

HRID 2228595Notes

Reaction equation

HRID 2228595 reaction equation
[O:1]1[C:5]([C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1>[OH-].[K+].C1COCC1>[O:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=2)=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 1477779Methyl 4-(1,3-oxazol-5-yl)benzoate

Product 1

HCID 27764144-(1,3-Oxazol-5-yl)benzoic Acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Procedure

The above ester was heated at reflux for 2 hours in a mixture of 1 M aqueous potassium hydroxide and 50 ml THF. The THF was removed in vacuo and the solution cooled, then acidified with 50% HCl to give 4-(1,3-oxazol-5-yl)benzoic acid as a white solid. NMR (300 MHz, DMSO-d6; 8.52 (s, 1H), 8.05 (d, 2H), 7.82-7.9, m, 3H).

Workup

  1. customThe THF was removed in vacuo
  2. temperaturethe solution cooled

Sources & evidence

ORD record
ord-638a5522ae174178913adaf6ab6a18b4
Source dataset
uspto-grants-2002_07
Patent number
US06417185B1

Reaction notes

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