Sodium Hydroxide → 2-Chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid

HRID 1276117Notes

Reaction equation

HRID 1276117 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:13]([C:14]2[CH2:18][CH:17]([CH3:19])[O:16][N:15]=2)=[C:12]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>CO>[Cl:3][C:4]1[C:13]([C:14]2[CH2:18][CH:17]([CH3:19])[O:16][N:15]=2)=[C:12]([S:20]([CH3:23])(=[O:21])=[O:22])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22114913Methyl 2-chloro-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate

Product 1

HCID 221149242-Chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3.52 g (88 mmol) of sodium hydroxide in 100 ml of methanol was slowly added dropwise to a mixture of 15.00 g (45 mmol) of methyl 2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate and 200 ml of methanol. The suspension was stirred at room temperature for 48 hours. The solvent was distilled off, the residue was taken up in water and the aqueous phase was washed three times with ethyl acetate. The aqueous phase was acidified with hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were subsequently washed neutral with water, dried and concentrated. 13.20 g (92% of theory) of 2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid were obtained.

Workup

  1. distillationThe solvent was distilled off
  2. washthe aqueous phase was washed three times with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b58a97322472437cac0737fe50f10f9d
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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