Sodium Hydroxide → HCID 178444403, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.55 g of β,β-dibromo-p-[2-(trans-4-pentylcyclohexyl)ethyl]styrene in 35 ml of absolute tetrahydrofuran was placed at about -45° C. in a sulphonation flask under argon gasification and treated within 5 minutes with 8.8 ml of a 1.2N solution of butyl lithium in hexane. After completion of the addition, the mixture was stirred at the same temperature for a further 90 minutes, then cooled to -78° C. and treated with 0.79 ml of phenyl cyanate. The mixture was subsequently stirred at -78° C. for a further 3 hours, then poured into 50 ml of 1N sodium hydroxide and extracted three times with 50 ml of diethyl ether/petroleum ether (1:1) each time. The organic phases were washed with 50 ml of 1N sodium hydroxide and 50 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (1.17 g) on silica gel with hexane followed by 3% ethyl acetate/petroleum ether gave 740 mg (69%) of p-[2-(trans-4-pentylcyclohexyl)ethyl]phenylpropiolonitrile as colourless crystals (purity 97.3%) which were recrystallized further from methanol; m.p. (C-N) 36.7° C., cl.p. (N-I) 105.5° C.

Provenance & Evidence