Sodium Hydroxide → 3-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)benzoic acid

HRID 1857314Notes

Reaction equation

HRID 1857314 reaction equation
[O:1]1[CH2:5][CH2:4][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+]>C(O)C>[O:1]1[CH2:5][CH2:4][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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22129428Methyl 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoate

Product 1

HCID 154774763-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)benzoic acidYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3.00 g of methyl 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoate were added 10 ml of ethanol and 20 ml of a 1N sodium hydroxide solution to stir at room temperature for 2 days. Ethanol was distilled out under reduced pressure. The remaining solution was 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 2.75 g of the title compound as white crystals. m.p. 182~184.5° C.

Workup

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

Sources & evidence

ORD record
ord-388a37b1693044d39a8176c90f5f6ac1
Source dataset
uspto-grants-2000_11
Patent number
US06147031

Reaction notes

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