Sodium Hydroxide → Sodium m-mesyloxybenzenesulfinate

HRID 67720Notes

Reaction equation

HRID 67720 reaction equation
S([O-])([O-])=O.[Na+:5].[Na+].[S:7]([O:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1)([CH3:10])(=[O:9])=[O:8].[OH-].[Na+]>O>[S:7]([O:11][C:12]1[CH:13]=[C:14]([S:18]([O-:20])=[O:19])[CH:15]=[CH:16][CH:17]=1)([CH3:10])(=[O:9])=[O:8].[Na+:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 13518302m-Mesyloxybenzenesulfonyl chloride

Product 1

HCID 23664830Sodium m-mesyloxybenzenesulfinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium sulfite (63 g; 0.5 mole) in water (400 ml) was added m-mesyloxybenzenesulfonyl chloride (67.7 g; 0.25 mole). The mixture was stirred vigorously, adding 50 percent sodium hydroxide solution as needed to maintain pH at 7 to 7.25, holding the temperature at 20° to 25° C. by means of a cold water bath. After 2 hours, a clear solution with a small amount of brown sludge was obtained. The mixture was filtered through Celite and the filtrate was poured into an evaporating dish and slowly allowed to evaporate. The first material to separate (32.5 g) was inorganic (by I. R. Spectrum). Further evaporation afforded three crops of crystalline material which was used without further purification.

Workup

  1. temperatureto maintain pH at 7 to 7.25
  2. customat 20° to 25° C.
  3. customa clear solution with a small amount of brown sludge was obtained
  4. filtrationThe mixture was filtered through Celite
  5. additionthe filtrate was poured into an evaporating dish
  6. customto evaporate
  7. customThe first material to separate (32.5 g)
  8. customFurther evaporation
  9. customafforded three crops of crystalline material which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-3ed4b08f74544cc0a31738c454122432
Source dataset
uspto-grants-1982_08
Patent number
US04346161

Reaction notes

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