Water → 4-Methylbenzenesulfonyl fluoride

HRID 1764050

Reaction equation

HRID 1764050 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.O.[F-:13].[K+]>C(#N)C>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([F:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 522689Potassium Fluoride

Product 1

HCID 99654-Methylbenzenesulfonyl fluoride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 25.0 gm (0.13 mole) portion of p-toluenesulfonyl chloride was dissolved in 100 ml of acetonitrile and combined in a 250 ml round bottom flask with 25.0 ml of water containing 1.5 gm (0.196 mole) of potassium fluoride. This mixture was stirred and heated under reflux for one hour. Acetonitrile was then removed under reduced pressure in a rotary evaporator. This resulted in crystallization of p-toluenesulfonyl fluoride which was removed by filtration, washed twice with water, and dried, giving 20.7 gm (91% yield) of product with mp 41°-41.2° C; (literature is 41°-42° C; W. Davies and J. H. Dick, J. Chem. Soc., 2104, 1931). The NMR and IR spectra were in agreement with the assigned structure.

Workup

  1. temperatureheated
  2. temperatureunder reflux for one hour
  3. customAcetonitrile was then removed under reduced pressure in a rotary evaporator

Sources & evidence

ORD record
ord-7e98772cc2bf4c8eabf5d36b11f11860
Source dataset
uspto-grants-1978_09
Patent number
US04115059

Linked notes

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