Chloride → HCID 18408283, compound

Participants

Reaction Steps

To 174 g (2.63 mol) of freshly depolymerized cyclopentadiene, cooled and maintained at -78 C, was added 87.5 g (2.50 mol) gaseous HCl. Meanwhile, 152 mL (1.0 mol) diethyl malonate was added to a solution of 21.4 g (0.93 mol) sodium in 400 mL absolute ethanol. After HCl addition to the cyclopentadiene was complete, the crude yellow chloride, maintained at -78 C, was added in mL portions to the malonate solution. With addition of each 1 ml portion of the malonate solution, considerable heat was produced, the yellow color rapidly dissipated, and copious white precipitate formed. After addition of all of the malonate, the suspension was stirred for 17 hrs, after which most of the ethanol was removed by rotary evaporation, and the reaction was quenched with 200 mL water and extracted 5 ×, each with 100 mL of diethyl ether. The combined extracts were dried over MgSO4, filtered, and concentrated to a clear yellow oil. Distillation of a portion of this material under 0.5 mm Hg pressure yielded 19.091 g clear, light green oil, bp 91-94 C.

Provenance & Evidence