Mesitylene → HCID 21863651, compound

HRID 2085905Notes

Reaction equation

HRID 2085905 reaction equation
[C:1]1([CH3:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:10]1([S:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[F:37][C:38]([F:44])([F:43])[S:39]([OH:42])(=[O:41])=[O:40]>CCCCCC>[F:37][C:38]([F:44])([F:43])[S:39]([O-:42])(=[O:41])=[O:40].[C:18]1([S+:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:2]2[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=2[CH3:9])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 7947MesityleneHCID 9845Trifluoroacetic anhydrideHCID 13679Diphenyl sulfoxideHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 21863651HCID 21863651, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

In 36.1 g (0.3 mole) of mesitylene was dissolved 6.1 g (0.03 mole) of diphenylsulfoxide, and 12.6 g (0.06 mole) of trifluoroacetic anhydride was poured thereinto under cooling at 5° C. or lower and further 4.5 g (0.03 mole) of trifluoromethane sulfonic acid was added dropwise thereto at −5 to 5° C., followed by allowing a reaction to take place at the same temperature for 2 hours with stirring. Into the resultant was poured 20 ml of n-hexane, followed by separation. This process step series was conducted three times and the resulting crude oily substance was crystallized from a mixture of butyl acetate and isopropyl ether and the crystal was recovered by filtration and dried to give 11.5 g (Yield: 84%) of diphenyl-2,4,6-trimethylphenylsulfonium trifluoromethanesulfonate as white crystal.

Workup

  1. additionwas poured
  2. customat −5 to 5° C.
  3. customa reaction
  4. customfor 2 hours
  5. customfollowed by separation
  6. customthe resulting crude oily substance was crystallized from a mixture of butyl acetate and isopropyl ether
  7. filtrationthe crystal was recovered by filtration
  8. customdried

Sources & evidence

ORD record
ord-c8cb5a2f9c514d19871231c5fc026a6e
Source dataset
uspto-grants-2004_04
Patent number
US06723483B1

Reaction notes

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