Toluene → 1,3-Diphenylpropane

Participants

Reaction Conditions

Reaction Steps

A dry oil jacketed reactor equipped with stainless steel internal cooling coils (chilled water) and a glass overhead stirring mechanism (no PTFE wetted parts) was charged with 4.325 kg (51.39 mol) of anhydrous toluene and heated to 80° C. To the mixture is charged butyl lithium (0.18 mol) in cyclohexane followed by 33.47 g (0.29 mol) dry TMEDA. Styrene (1.5 g, 14.4 mol) was fed to the reactor (through a plug of anhydrous basic alumina) in 150 minutes at 90-95° C. The reaction mixture was quenched with 100 mL of water and subsequently washed three times with 0.5 kg of tap water. Toluene was distilled from the crude oligomers. The crude material was then distilled at full vacuum to yield 2.0 kg of 1,3-diphenylpropane, 300 g of 1,3,5-triphenylpentane, 120 g of 1,3,5,7-tetraphenylheptane and 8 grams of undistillable oligomer bottoms.

Provenance & Evidence