Triphenyl phosphite → 4-(4-propylcyclohexyl)cyclohexyl-2Z-butene

Participants

Reaction Steps

Into a flask, were placed triphenylphosphite (2.6 g, 10 mmol) and 4-bromophenethylbromide (2.6 g, 10 mmol) prepared from 4-bromophenethylalcohol, followed by adding and dissolving xylene (10 ml), heating under reflex for 10 hours after the completion of reaction, filtering off the deposited white crystals of 4-bromo-phenethyltriphenylphosphoniumbromide, and drying the white crystals (5.1 g, 9.5 mmol). The obtained white crystals were dissolved into THF (30 ml), followed by stirring under ice cooling, adding potassium-t-butoxid (1 g, 9 mmol) slowly into the reaction solution, stirring the solution at room temperature for 2 hours after the completion of dropping, adding THF (20 ml) solution of 4-(4-propylcyclohexyl)cyclohexylacetaldehyde (2.2 g, 9 mmol), further stirring for 5 hours, adding ether after the completion of reaction, filtrating off white solid deposited, concentrating the filtrate under reduced pressure, purifying the obtained brown oil by means of silica gel chromatography, to obtain a mixture (2.2 g, 5.3 mmol) of 1-(4-bromophenyl)-4-(4-(4-propylcyclohexyl)cyclohexyl-2Z-butene with its E-isomer.

Provenance & Evidence