Hexane → HCID 178445604, compound

Participants

Reaction Conditions

Reaction Steps

A solution, cooled to -20° C., of 398 g of tetrabromomethane in 1 l of methylene chloride was treated dropwise under nitrogen gasification within 30 minutes with a solution of 629.6 g of triphenylphosphine in 1 l of methylene chloride. The mixture was subsequently stirred at -10° C. for a further 30 minutes, then treated dropwise within 30 minutes with a solution of 101 g of trans-4-butylcyclohexanecarboxaldehyde in 500 ml of methylene chloride and stirred at -5° C. for a further 2 hours. The mixture was poured into 4 l of hexane, the resulting mixture was stirred at -20° C. for 1 hour and then the precipitate was filtered off under suction and rinsed well with 1 l of cold (-20° C.) hexane. The filtrate was concentrated to a volume of about 1 l on a rotary evaporator, diluted with 2 l of hexane, again concentrated to a volume of about 1 l and stirred at -20° C. for a further 30 minutes. The precipitate was filtered off under suction and rinsed well with 700 ml of cold (-20° C.) hexane. The filtrate was freed from solvent on a rotary evaporator and the resulting yellow oil (195 g) was filtered chromatographically on silica gel with about 3 l of hexane. The eluate was evaporated up to constant weight on a rotary evaporator, there being obtained 171.3 g (88.1%) of trans-1-(2,2-dibromovinyl)-4-butylcyclohexane as a colourless liquid; Rf-value (hexane) 0.55.

Provenance & Evidence