Hydrochloric Acid → 3-(4-Methylphenyl)isoxazole-4-carboxylic acid

HRID 2110998Notes

Reaction equation

HRID 2110998 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([C:7]2[C:11]([C:12]([O:14]C)=[O:13])=[CH:10][O:9][N:8]=2)=[CH:3][CH:2]=1.[OH-].[Li+].Cl>C1COCC1>[C:1]1([CH3:16])[CH:2]=[CH:3][C:4]([C:7]2[C:11]([C:12]([OH:14])=[O:13])=[CH:10][O:9][N:8]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 870147HCID 870147, compound

Product 1

HCID 588287973-(4-Methylphenyl)isoxazole-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-p-tolyl-isoxazole-4-carboxylate (3.1 g, 14.3 mmol) was dissolved in THF (50 ml), 2N aqueous lithium hydroxide solution (50 ml) was added, and the mixture was stirred for 4 hours. Then, 1N hydrochloric acid (150 ml) was added at 0° C., and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.89 g, 14.3 mmol, 100%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5d2b6043cf1447169ac96f4964bd6186
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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