Phenacyl bromide → HCID 16688854, compound

Participants

Reaction Steps

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.

Provenance & Evidence