Benzene → Dibenzyl

Participants

Reaction Steps

To a dry, nitrogen-filled 250 ml single-necked round-bottom flask fitted with a nitrogen inlet and magnetic stirring bar was added 11.8 g (65.5 mmol) of stilbene, 11 g (240 mmol) formic acid, 5 g of 10% Pd on activated carbon (4.7 mmol Pd), 60 ml of absolute ethanol and 100 ml of dry benzene. The reaction vessel was placed in a sonicator so that the liquid level inside the flask matched that of the bath water and in the location that produced the maximum cavitation in the flask. After 1 h the flask was removed and the contents filtered. The solid was washed with chloroform and the combined filtrates concentrated on a rotary evaporator. The residual soild was recrystallized (ethanol-pentane) to give 11.03g (92.5% yield) of bibenzyl mp 51°-51.5° (lit 52.5) (8).

Provenance & Evidence