Sodium Hydroxide → 5-Methyl-3-phenylisoxazole-4-carboxylic acid

HRID 2120856

Reaction equation

HRID 2120856 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=[O:4].[OH-].[Na+]>CO.O>[CH3:10][C:9]1[O:8][N:7]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]=1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 727920Methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate

Product 1

HCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 5-Methyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester (0.853 g, 3.69 mmol) in methanol (12 mL) was added 2N NaOH (8 mL) the reaction solution was stirred at ambient temperature for 60 hr. The solution was dilute with water and extracted twice with ethyl acetate. The combined extract was washed with brine and dried over MgSO4 and concentrated. Recrystallization (hexanes/ethyl acetate) afforded a white solid (0.540 g, 72% yield).

Workup

  1. extractionextracted twice with ethyl acetate
  2. extractionThe combined extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customRecrystallization (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-759782c99ed64ee299dbfffe8399244d
Source dataset
uspto-grants-2004_02
Patent number
US06693108B2

Linked notes

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