Cyclopentadiene → HCID 14094221, compound

Participants

Reaction Conditions

Reaction Steps

A double-walled reactor having a volume of 1.5 L, provided with baffles, condenser, top stirrer, thermometer and dropping funnel, was charged with 900 g of clear 50% strength NaOH (11.3 mol), followed by cooling to 10° C. Then 30 g of Aliquat 336 (74 mmol) and 48 g (0.72 mol) of freshly cracked cyclopentadiene were added. The reaction mixture was stirred vigorously for a few minutes, then 577 g of octyl bromide (2.99 mol) were added over a period of one hour, while the reaction mixture was cooled with circulating water at 10° C. After one hour of stirring at room temperature, the reaction mixture was heated to 35° C., followed by a further 6 hours of stirring. Stirring was stopped and phase separation was performed. The aqueous layer was drawn off and 920 g (11.5 mol) of fresh 50% strength NaOH were added, followed by a further 5 hours of stirring at room temperature. GC was used to show that 10% of tri-, 83% of tetra- and 7% of penta(octyl)cyclopentadiene were present in the mixture. The product was distilled under reduced pressure. After vacuum distillation, 226.6 g of tetra(octyl)cyclopentadiene were obtained, which was characterized with GC, GC-MS, 13C- and 1H-NMR.

Provenance & Evidence