Reaction #465673

Reaction equation

sodium bromide

phenacyl bromide

sodium hexafluoroantimonate

methyl octadecyl sulfide

→

desired salt

Methyl Octadecylphenacylsulfonium Hexafluoroantimonate

Solvents

methyl ethyl ketone

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated
2. 2
   Temperaturemaintained at this temperature for 30 minutes
3. 3
   Otherto precipitate
4. 4
   FiltrationThe reaction mixture was filtered
5. 5
   Otherto remove the inorganic salts
6. 6
   Otherthe resulting solution placed on a rotary evaporator
7. 7
   Otherto remove solvents
8. 8
   OtherThe product crystallized

Procedure

In a 100 mL Erlenmeyer flask were combined 10 g (0.05 mol) phenacyl bromide, 12.93 g (0.05 mol) sodium hexafluoroantimonate, 15 g (0.05 mol) methyl octadecyl sulfide and 40 mL methyl ethyl ketone (2-butanone). The reaction mixture was heated to boiling and maintained at this temperature for 30 minutes. During this time, sodium bromide was observed to precipitate. The reaction mixture was filtered to remove the inorganic salts and the resulting solution placed on a rotary evaporator to remove solvents. The product crystallized to give the desired salt, m.p. 80-82° C. Recrystallization from isopropanol gave a very light tan salt with a melting point of 79-80° C.

Source