Reaction #465674

Reaction equation

methyl octyl sulfide

phenacyl bromide

sodium hexafluoroantimonate

→

methyl octylphenacylsulfonium hexafluoroantimonate

Yield 83.7%

Solvents

acetone

Conditions

Workup

1. 1
   OtherInto a 100 mL round bottom flask equipped with a magnetic stirrer
2. 2
   Temperaturereflux condenser
3. 3
   Otherobtained from the Aldrich Chemical Co
4. 4
   Temperatureto reflux
5. 5
   FiltrationThe mixture was filtered through a plug of glass wool (
6. 6
   Otherto remove the sodium bromide which
7. 7
   Otherwas formed during the reaction) and the solvent
8. 8
   Otherwas removed on a rotary evaporator

Procedure

Into a 100 mL round bottom flask equipped with a magnetic stirrer and reflux condenser were placed 16.0 g (0.1 mol) methyl octyl sulfide (obtained from the Aldrich Chemical Co.), 19.9 g (0.1 mol) phenacyl bromide, 25.87 g (0.1 mol) sodium hexafluoroantimonate and 40 mL acetone. The reaction mixture was brought to reflux and held at this temperature for 15 minutes. The mixture was filtered through a plug of glass wool (to remove the sodium bromide which was formed during the reaction) and the solvent was removed on a rotary evaporator, leaving 43.1 g (83.6% yield) of the desired methyl octylphenacylsulfonium hexafluoroantimonate as a tan colored solid. The product was further purified by recrystallization, first from a 1:3 mixture of water and ethanol, then, isopropanol. The pure, colorless, crystalline initiator had a melting point of 75-76° C. The initiator was soluble in a wide variety of common solvents such as acetone, methyl ethyl ketone, chloroform and methylene chloride.

Source