Sulfuric Acid → HCID 89511128, compound

HRID 469136Notes

Reaction equation

HRID 469136 reaction equation
[S:1](=[O:5])(=O)([OH:3])[OH:2].[F:6][C:7]([F:18])([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:8]([F:10])[F:9].[OH-].[Na+:20]>>[F:6][C:7]([F:18])([O:11][C:12]1[CH:13]=[CH:14][C:15]([S:1]([O-:3])(=[O:5])=[O:2])=[CH:16][CH:17]=1)[CH:8]([F:9])[F:10].[Na+:20]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67692(1,1,2,2-Tetrafluoroethoxy)benzene

Product 1

HCID 89511128HCID 89511128, compoundYield 59%

Procedure

A 50 mL flask equipped with a stir-bar and a nitrogen bubbler was charged with concentrated sulfuric acid (14.55 g) and 4-(1,1,2,2-tetrafluoroethoxy)benzene (4.9 g) at room temperature. The reaction mixture was stirred at room temperature for 17 h. A sodium hydroxide solution (12.25 g, in 40.02 g water) was slowly added to the reaction mixture while the reaction mixture was cooled with an ice-water bath. The resulting solid was filtered off. The filtrate was neutralized with concentrated hydrochloric acid (˜3 mL) and used to wash the solid. This wash solution was neutralized with sodium bicarbonate to pH˜7, and used to wash the solid again. The solid was extracted with refluxing ethanol. The ethanol solution was dried to give sodium 4-(1,1,2,2-tetrafluoroethoxy)benzenesulfonate (4FEBSNa) 4.4 g (yield 59%): 1H NMR (D2O) 6.34 (tt, 52, 3 Hz, 1H), 7.45 (d, J=9 Hz, 2H), 7.88 (m, 2H) ppm; 19F NMR (D2O) −88.7 (m, 2F), −138.0 (dt, J=52, 5 Hz, 2F) ppm.

Workup

  1. customA 50 mL flask equipped with a stir-bar
  2. temperaturewas cooled with an ice-water bath
  3. filtrationThe resulting solid was filtered off
  4. washto wash the solid
  5. washto wash the solid again
  6. extractionThe solid was extracted with refluxing ethanol
  7. dry with materialThe ethanol solution was dried

Sources & evidence

ORD record
ord-77ddb38be03e48aaa63afe0a03bfb41b
Source dataset
uspto-grants-2014_01
Patent number
US08628682B2

Reaction notes

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