Acetophenone → 3-(Methylsulfanyl)-1,5-diphenylpent-2-ene-1,5-dione

Participants

Reaction Conditions

Reaction Steps

Ketene dithioacetal (Product A) (2.0 g, 0.0089 mol) was added to a solution of acetophenone (1.07 g, 0.0089 mol) and potassium tert-butoxide (2.0 g, 0.0178 mol) in dry THF (20 mL). The temperature of the reaction mixture was raised to 60° C. and the mixture was stirred for 1 hour during which time an orange-red precipitate formed. This was collected and added to an ice-cold HCl solution (4% acid) and the oily material which separated allowed to crystallize. The brown solid was collected and recrystallized from benzene: petroleum ether (b.p. 80°-100° C.) from which it separated as pale-yellow prisms: 1.8 g (70%), m.p. 106°-108° C.: IR (KBr)νCO 1680, 1630 cm-1 ; NMR (CDCl3)δ8.0-7.56 (m, 10, aromatic), 6.82 (s,1, vinylic), 4.64 (s,2,CH2), 2.59 (s,3,SCH3); M.+ 296 (7%).

Provenance & Evidence