Phenylmethylsulfonyl Fluoride → Potassium alpha-toluenesulfonate

HRID 3956

Reaction equation

HRID 3956 reaction equation
[C:1]1([CH2:7][S:8](F)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[O-:14].[K+:17]>O1CCCC1>[C:1]1([CH2:7][S:8]([O-:10])(=[O:14])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K+:17]

Participants

4

Reactant 2

HCID 4784Phenylmethylsulfonyl FluorideHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 23666503Potassium alpha-toluenesulfonateYield 58.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The procedure of Example 1 was followed using α-toluenesulfonyl fluoride (2.0 g, 11.5 mmol) in dry tetrahydrofuran (15 mL), potassium trimethylsilanolate (1.48 g, 11.5 mmol) and dry tetrahydrofuran (45 mL), and 2 h of heating at reflux. Potassium α-toluenesulfonate (1.41 g, 58% yield) was isolated as a white solid: 1H NMR (D2O) δ 4.1 (s, CH2, 2H), 7.4 ppm (s, Ar--H's, 5H).

Workup

  1. temperatureof heating
  2. temperatureat reflux

Sources & evidence

ORD record
ord-38f5d19da7814e449f56363466a7475c
Source dataset
uspto-grants-1988_02
Patent number
US04723016

Linked notes

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