Sodium Hydroxide → 2-Chloro-3-(5-benzylisoxazolin-3-yl)4-methylsulfonylbenzoic acid

HRID 322059Notes

Reaction equation

HRID 322059 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH2:16][CH:15]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:14][N:13]=2)=[C:10]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[C:11]([C:12]2[CH2:16][CH:15]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:14][N:13]=2)=[C:10]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22009884Methyl 2-chloro-3-(5-benzylisoxazolin-3-yl)-4-methylsulfonylbenzoate

Product 1

HCID 220098852-Chloro-3-(5-benzylisoxazolin-3-yl)4-methylsulfonylbenzoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.02 g (2.5 mmol) of methyl 2-chloro-3-(5-benzylisoxazolin-3-yl)-4-methylsulfonylbenzoate are dissolved in 20 ml of methanol and combined with 0.15 g (3.7 mmol) of sodium hydroxide—dissolved in 10 ml of water—at room temperature. After 16 hours, the methanol is removed by distillation, the residue is diluted with water and, after acidifying to pH 2, the mixture is extracted with dichloromethane. After concentrating in a rotary evaporator, 0.85 g (87% of theory) of 2-chloro-3-(5-benzylisoxazolin-3-yl)4-methylsulfonylbenzoic acid is obtained as a yellowish resin.

Workup

  1. customthe methanol is removed by distillation
  2. additionthe residue is diluted with water
  3. extractionthe mixture is extracted with dichloromethane
  4. concentrationAfter concentrating in a rotary evaporator

Sources & evidence

ORD record
ord-f376a8b889264354adea60e188e94d66
Source dataset
uspto-grants-2001_04
Patent number
US06211216B1

Reaction notes

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