Reaction #52135

Reaction equation

1,3,5-trimethylbenzene

diphenylsulfoxide

Eaton's Reagent

→

2,4,6-trimethylphenyldiphenylsulfonium mesylate

Solvents

water

Conditions

Workup

1. 1
   OtherIn a 1 L, round bottom flask equipped with a reflux condenser
2. 2
   OtherAn exothermic reaction
3. 3
   workup.STIRRINGThis mixture was stirred for 30 minutes
4. 4
   ExtractionThe mixture was extracted two times with toluene (2×250 mL)
5. 5
   workup.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)

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).

Source