Sodium Hydroxide → 2-Chloro-4-methylsulfonyl-3-(3a,4,5,6a-tetrahydrofuro[3,2-d]isoxazol-3-yl)benzoic acid

HRID 48143Notes

Reaction equation

HRID 48143 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH:16]3[CH2:17][CH2:18][O:19][CH:15]3[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]3[CH2:17][CH2:18][O:19][CH:15]3[O:14][N:13]=2)=[C:10]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22742138HCID 22742138, compound

Product 1

HCID 227421292-Chloro-4-methylsulfonyl-3-(3a,4,5,6a-tetrahydrofuro[3,2-d]isoxazol-3-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

60.0 g (168.8 mmol) of methyl 2-chloro-4-methylsulfonyl-3-(3a,4,5,6a-tetrahydrofuro[3,2-d]isoxazol-3-yl)benzoate are dissolved in 600 ml of tetrahydrofuran/300 ml of water, and 7.34 g (183.4 mmol) of sodium hydroxide are added. After the reaction mixture has been stirred for 18 hours at room temperature, it is concentrated, brought to pH 2 with 2 N hydrochloric acid and extracted with dichloromethane. This gives 63.6 g of crude 2-chloro-4-methylsulfonyl-3-(3a,4,5,6a-tetrahydrofuro[3,2-d]isoxazol-3yl)benzoic acid as a foam.

Workup

  1. additionare added
  2. concentrationit is concentrated
  3. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-208b3846e3e94446994a0ea9c9bc2487
Source dataset
uspto-grants-2004_03
Patent number
US06703348B2

Reaction notes

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