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

HRID 2167427Notes

Reaction equation

HRID 2167427 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 acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3.52 g (88 mmol) of sodium hydroxide, dissolved 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 for 48 hours at room temperature. After the solvent had been 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 to neutrality with water, dried and concentrated. This gave 13.20 g (92% of theory) of 2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid.

Workup

  1. distillationAfter the solvent had been distilled off
  2. washthe aqueous phase was washed three times with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were subsequently washed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e004b640b8d44b769a60b055675032cf
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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