Cyclopentadiene → HCID 14094221, compound

Participants

Reaction Conditions

Reaction Steps

A 1.5 L double-walled reactor, provided with baffles, condenser, top stirrer, thermometer and dropping funnel was charged with 900 g of 50 wt. % 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 turbulently for a few minutes. Then 577 g of octyl bromide (2.99 mol) were added in one hour, cooling with water taking place at the same time. After 1 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 awaited. The aqueous layer was drawn off and 920 g (11.5 mol) of fresh 50 wt. % NaOH were added, followed by a further 5 hours of stirring at room temperature. GC was used to show that after 5 hours 10% of tri-, 83% of tetra- and 7% of penta(octyl)cyclopentadiene were present in the mixture. The product was distilled at reduced pressure. After vacuum distillation, 226.6 g of tetra(octyl)cyclopentadiene were obtained. Characterization of the product took place with the aid of GC, GC-MS, 13C- and 1H-NMR.

Provenance & Evidence