Reaction #1973310

ord-c4a427ff18f14e458ca879412bd0cf43

Reaction equation

C
charcoal
[F][Sb-]([F])([F])([F])([F])[F].[Na+]
sodium hexafluoroantimonate
O=S(=O)([O-])O.c1ccc(C[S+](Cc2ccccc2)Cc2ccccc2)cc1
tribenzylsulfonium hydrogen sulfate
[F][Sb-]([F])([F])([F])([F])[F].c1ccc(C[S+](Cc2ccccc2)Cc2ccccc2)cc1
tribenzylsulfonium hexafluoroantimonate
Yield 74.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Filtrationthe mixture is filtered
  2. 2
    workup.ADDITION750 ml of water are added to the clear filtrate
  3. 3
    OtherThe crystals which have precipitated
  4. 4
    Filtrationare filtered off
  5. 5
    Otherdried
  6. 6
    Washwashed with 100 ml of ether
  7. 7
    Otherdried again

Procedure

16.64 g (0.041 mol) of tribenzylsulfonium hydrogen sulfate are dissolved in 750 ml of hot methanol. 16.04 g (0.062 mol) of solid sodium hexafluoroantimonate are added to the cloudy solution and the mixture is stirred at RT for 1 h. After addition of 1 spatula-full of active charcoal, the mixture is filtered and 750 ml of water are added to the clear filtrate. The crystals which have precipitated are filtered off, dried, washed with 100 ml of ether and dried again. 16.41 g (74% of theory) of tribenzylsulfonium hexafluoroantimonate are obtained as colourless crystals of melting point 170° C. (decomposition).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05149767uspto-grants-1992_09