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

HRID 322056Notes

Reaction equation

HRID 322056 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH:16]=[C:15]([CH2:17][O:18][CH3:19])[O:14][N:13]=2)=[C:10]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[C:11]([C:12]2[CH:16]=[C:15]([CH2:17][O:18][CH3:19])[O:14][N:13]=2)=[C:10]([S:20]([CH3:23])(=[O:21])=[O:22])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22009882Methyl 2-chloro-3-(5-methoxymethylisoxazol-3-yl)-4-methylsulfonylbenzoate

Product 1

HCID 220098912-Chloro-3-(5-methoxymethylisoxazol-3-yl)-4-methylsulfonylbenzoic acidYield 94.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.23 g (3.4 mmol) of methyl 2-chloro-3-(5-methoxymethylisoxazol-3-yl)-4-methylsulfonylbenzoate are dissolved in 30 ml of tetrahydrofuran/20 ml of water and treated with 0.15 g (3.8 mmol) of sodium hydroxide. After stirring at room temperature for 18 hours, the reaction mixture is concentrated, adjusted to pH 2 using 2N hydrochloric acid and extracted with dichloromethane. 1.05 g (94.8% of theory) of 2-chloro-3-(5-methoxymethylisoxazol-3-yl)-4-methylsulfonylbenzoic acid are obtained as a yellowish oil.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-0134b1143ae645c09664aa5846220ed3
Source dataset
uspto-grants-2001_04
Patent number
US06211216B1

Reaction notes

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