Lithium hydroxide, monohydrate → 3-(4-Chloromethylphenyl)isoxazole-4-carboxylic acid

HRID 2111004Notes

Reaction equation

HRID 2111004 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][O:11][N:10]=2)=[CH:5][CH:4]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][O:11][N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 45117061HCID 45117061, compound

Product 1

HCID 688820423-(4-Chloromethylphenyl)isoxazole-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 3-(4-chloromethylphenyl)isoxazole-4-carboxylate (7.59 g, 30.16 mmol) was dissolved in THF-water (2:1, 225 ml), lithium hydroxide monohydrate (5.06 g, 120.6 mmol) was added, and the mixture was stirred at room temperature for 6 hours. THF was evaporated under reduced pressure, 2N hydrochloric acid was added to weakly acidify the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (7.14 g, 100%).

Workup

  1. customTHF was evaporated under reduced pressure, 2N hydrochloric acid
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7830ff47f8b24f0c9c65f2490dd9c48d
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

Loading…