Sodium Hydroxide → Sodium 4-(trifluoromethoxy)benzenesulfonate

HRID 469135

Reaction equation

HRID 469135 reaction equation
[F:1][C:2]([F:11])([F:10])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH:12][S:13](O)(=[O:15])=[O:14].O=S(=O)=O.[OH-].[Na+:22]>>[F:1][C:2]([F:10])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:13]([O-:15])(=[O:14])=[O:12])=[CH:6][CH:5]=1.[Na+:22]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24681Fuming sulfuric acidHCID 68010(Trifluoromethoxy)benzene

Product 1

HCID 89511132Sodium 4-(trifluoromethoxy)benzenesulfonateYield 24%

Procedure

A 100 mL flask equipped with a stir-bar and a nitrogen bubbler was charged with (trifluoromethoxy)-benzene (5.015 g) at room temperature. Oleum (15% SO3, 9.30 g) was added to the above flask at 10° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 15 h. A sodium hydroxide solution (7.75 g, in 23 mL water) was slowly added to the reaction mixture while the reaction mixture was cooled with an ice-water bath. The resulting solid was collected by filtration, dried under vacuum, and then extracted with refluxing ethanol. The ethanol solution was dried to give sodium 4-(trifluoromethoxy)benzenesulfonate (3FMBSNa) 2.0 g (yield 24%): 1H NMR (D2O) 7.45 (d, J=9 Hz, 2H), 7.89 (m, 2H) ppm; 19F NMR (D2O)-58.1 (s) ppm.

Workup

  1. customA 100 mL flask equipped with a stir-bar
  2. temperaturewas cooled with an ice-water bath
  3. filtrationThe resulting solid was collected by filtration
  4. customdried under vacuum
  5. extractionextracted with refluxing ethanol
  6. dry with materialThe ethanol solution was dried

Sources & evidence

ORD record
ord-997842f8c1d54d878c1a82838cad9e3e
Source dataset
uspto-grants-2014_01
Patent number
US08628682B2

Linked notes

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