Water → 2-(5-Oxazolyl)benzoic Acid

HRID 717295Notes

Reaction equation

HRID 717295 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-5a64fc14107042d18a59b6140cdec96e
Source dataset
uspto-grants-2015_11
Patent number
US09193709B2

Reaction notes

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