Water → 2-(5-Oxazolyl)benzoic Acid

HRID 240400Notes

Reaction equation

HRID 240400 reaction equation
[O:1]1[C:5]([C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=2[C:8]([O:10]C)=[O:9])=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].O>C1COCC1>[O:1]1[C:5]([C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=2[C:8]([OH:10])=[O:9])=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 73553912Methyl 2-(5-Oxazolyl)benzoate

Product 1

HCID 533937912-(5-Oxazolyl)benzoic AcidYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(1,3-oxazol-5-yl)benzoate (4.0 g) in THF (40 mL) was added 2 N aqueous sodium hydroxide solution (20 mL), and the mixture was stirred at room temperature stirred for 2 days. To the reaction mixture was added water, and the mixture was washed with tert-butyl methyl ether. The pH of the obtained aqueous layer was adjusted to 2 with 2N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate/petroleum ether to give the title compound (3.3 g).

Workup

  1. stirringstirred for 2 days
  2. washthe mixture was washed with tert-butyl methyl ether
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washThe residue was washed with ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-3b83ad58f7e0401994c099d3c6e9b76f
Source dataset
uspto-grants-2014_02
Patent number
US08648079B2

Reaction notes

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