Water → 3-Methyl-1,2-oxazole-4-carboxylic acid

HRID 480088

Reaction equation

HRID 480088 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][O:4][N:3]=1.O>C(O)C.[OH-].[Na+]>[CH3:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][O:4][N:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 317668Ethyl 3-methyl-1,2-oxazole-4-carboxylate

Product 1

HCID 45896923-Methyl-1,2-oxazole-4-carboxylic acidYield 93.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 3-methyl-4-isoxazolecarboxylate (1.3 g) is stirred at room temperature overnight in 5 mL of ethanol and 10 mL of 2.5 N sodium hydroxide. Dilution with water, cooling in ice, and acidification to pH 2 with 6 N hydrochloric acid precipitates an off-white solid which is collected by vacuum filtration, washed with ethanol/water, and dried under vacuum to give 1.0 g of 3-methyl-4-isoxazolecarboxylic acid.

Workup

  1. customacidification to pH 2 with 6 N hydrochloric acid precipitates an off-white solid which
  2. filtrationis collected by vacuum filtration
  3. washwashed with ethanol/water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f0a771454ca241ffaf8ed8222497cba7
Source dataset
uspto-grants-2003_11
Patent number
US06649635B2

Linked notes

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