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

HRID 1375633

Reaction equation

HRID 1375633 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-b96d7a5e95cf41579c754086b5928b63
Source dataset
uspto-grants-2007_01
Patent number
US07169798B2

Linked notes

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