Diphenylmethane → HCID 21964751, compound

HRID 2212624Notes

Reaction equation

HRID 2212624 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[F:41][C:42]([F:48])([F:47])[S:43]([OH:46])(=[O:45])=[O:44]>CCCCCC.O>[F:41][C:42]([F:48])([F:47])[S:43]([O-:46])(=[O:45])=[O:44].[C:9]1([S+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:18]2[CH:19]=[CH:20][C:15]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:16][CH:17]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 7580DiphenylmethaneHCID 9845Trifluoroacetic anhydrideHCID 13679Diphenyl sulfoxideHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 21964751HCID 21964751, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

In 35 ml of n-hexane were suspended 6.07 g (0.03 mol) of diphenylsulfoxide and 6.06 g (0.036 mol) of diphenylmethane, and 7.56 g (0.036 mol) of trifluoroacetic anhydride was added thereto at 0° C. Then 4.5 g (0.03 mol) of trifluoromethanesulfonic acid was added dropwise thereto at 0 to 5° C., followed by gradually warming to room temperature and reacting for 4 hours with stirring. After completion of the reaction, 50 ml of water was poured into the reaction solution and the n-hexane layer was removed by fractionation. The aqueous layer was further washed with 50 ml of hexane three times and extracted with 60 ml of dichloromethane. The resulting dichloromethane layer was washed with 50 ml of water five times, followed by concentration under reduced pressure. 70 ml of ethyl acetate was poured into the resulting crude crystal, followed by dissolving by warming to 60° C., cooling to room temperature, the resulting crude crystal was filtered and dried under vacuum to obtain 11.3 g (Yield: 75%) of diphenyl-4-phenylmethylphenylsulfonium trifluoromethanesulfonate as a pale brown crystal.

Workup

  1. additionwas added
  2. customat 0° C
  3. customat 0 to 5° C.
  4. additionwas poured into the reaction solution
  5. customthe n-hexane layer was removed by fractionation
  6. washThe aqueous layer was further washed with 50 ml of hexane three times
  7. extractionextracted with 60 ml of dichloromethane
  8. washThe resulting dichloromethane layer was washed with 50 ml of water five times
  9. concentrationfollowed by concentration under reduced pressure
  10. addition70 ml of ethyl acetate was poured into the resulting crude crystal
  11. dissolutionby dissolving
  12. temperatureby warming to 60° C.
  13. temperaturecooling to room temperature
  14. filtrationthe resulting crude crystal was filtered
  15. customdried under vacuum

Sources & evidence

ORD record
ord-8959bfd50d794ea18d3cb0a01f028bce
Source dataset
uspto-grants-2006_09
Patent number
US07101918B2

Reaction notes

Loading…