Mesitylene → 2,4,6-Trimethylphenyldiphenylsulfonium mesylate

HRID 23857

Reaction equation

HRID 23857 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=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.[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[S:25]([O-:28])(=[O:27])(=[O:26])[CH3:24].[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S+:16]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7947MesityleneHCID 13679Diphenyl sulfoxideHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 223863512,4,6-Trimethylphenyldiphenylsulfonium mesylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
52.5 °C

Procedure

In a 1 L, round bottom flask equipped with a reflux condenser was combined 1,3,5-trimethylbenzene (40 g, 0.333 mol), diphenylsulfoxide (67.3 g, 0.333 mol) and Eaton's Reagent (160 g). An exothermic reaction occurred. The reaction mixture was maintained at 50-55° C. with stirring for 5 hours. The reaction mixture was then added to deionized water (800 mL). This mixture was stirred for 30 minutes. The mixture was extracted two times with toluene (2×250 mL). The pH of the lower aqueous layer was adjusted to 8-8.5 by addition of a 25% aqueous solution of tetramethylammonium hydroxide (889.6 g).

Workup

  1. customIn a 1 L, round bottom flask equipped with a reflux condenser
  2. customAn exothermic reaction
  3. stirringThis mixture was stirred for 30 minutes
  4. extractionThe mixture was extracted two times with toluene (2×250 mL)
  5. additionThe pH of the lower aqueous layer was adjusted to 8-8.5 by addition of a 25% aqueous solution of tetramethylammonium hydroxide (889.6 g)

Sources & evidence

ORD record
ord-51dabc49019643fd984289bdf9d1ebb7
Source dataset
uspto-grants-2005_02
Patent number
US06855476B2

Linked notes

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