Hydrochloric Acid → 3-(Isoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid

HRID 1857316Notes

Reaction equation

HRID 1857316 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([CH3:20])=[C:8]([CH:13]=[CH:14][C:15]=2[S:16]([CH3:19])(=[O:18])=[O:17])[C:9]([O:11]C)=[O:10])=[N:2]1.[OH-].[Na+].Cl>C(O)C>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([CH3:20])=[C:8]([CH:13]=[CH:14][C:15]=2[S:16]([CH3:19])(=[O:18])=[O:17])[C:9]([OH:11])=[O:10])=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22129427Methyl 3-(isoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoate

Product 1

HCID 221294303-(Isoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acidYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 0.80 g of methyl 3-(isoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoate were added 8 ml of ethanol and 8 ml of a 1N sodium hydroxide solution to stir at room temperature for 2 days. The reaction solution was poured into ice water, acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, then with a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure to give 0.56 g of the title compound as white crystals. m.p. 150-151° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-25d3a024a79d43828b631de44da7bae9
Source dataset
uspto-grants-2000_11
Patent number
US06147031

Reaction notes

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