Hydrochloric Acid → HCID 59408360, compound

Participants

Reaction Steps

3.5 g (11.3 mmol) of 4-ethynyl-4′-(4-propylphenyl)bicyclohexyl are initially introduced in 30 ml of THF at −20° C., and 8.6 ml (13.6 mmol) of n-BuLi (15% soln. in hexane) are added dropwise. After 1 h at this temperature, 0.85 ml (13.6 mmol) of methyl iodide is metered in, and the batch is left in the cooling bath to thaw for 3 h. Water and dil. hydrochloric acid are added, and the mixture is extracted a number of times with MTBE. The combined organic phases are washed with water and sat. sodium chloride soln., and the solution is dried using sodium sulfate. The crude product obtained after removal of the solvents is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=4:1). The further purification is carried out by recrystallisation from n-heptane. This gives 4′-(4-propylphenyl)-4-prop-1-ynylbicyclohexyl as a colourless solid having an m.p. of 70° C.

Provenance & Evidence