Hexanal → HCID 67526844, compound

Participants

Reaction Steps

Sodium (27.6 g, 1.2 mol) is dissolved in methanol (550 ml) and benzyl cyanide (140.4 g, 1.2 mol) is added, followed by dropwise addition over 45 min. of hexanal (164.2 g, 1.44 mol), keeping the inside temperature between 20-25° C. The mixture is further stirred during 90 min. at room temperature, and then extracted 3 times with hexane. The organic layers are washed with water, 2 N aq. HCl-solution, then brine. The organic layer is dried over MgSO4, the solvent removed under reduced pressure and the residue distilled over a short-path apparatus at 0.04 mbar. The fraction distilling at 114-121° C. is collected (172 g) and subjected to a fine distillation over a Widmer-column to yield olfactorily pure 2-phenyl-oct-2-ene nitrile (113 g, 44%) as a colourless oil (b.p. 113-115° C./0.03 mbar).

Provenance & Evidence