Cyclopentadiene → HCID 53827973, compound

Participants

Reaction Conditions

Reaction Steps

A 1 L double-walled reactor, provided with baffles, condenser, top stirrer, thermometer and dropping funnel was charged with 430 g (5.4 mol) of 50 wt. % NaOH. Then 23 g of ALIQUAT 336 (57 mmol) and 27 g (0.41 mol) of freshly cracked cyclopentadiene were added. The reaction mixture was stirred turbulently for a few minutes. Then 150 g of 3-pentyl bromide (1.0 mol) were added over a period of 1 hour, cooling with water taking place at the same time. After 1 hour of stirring at room temperature the reaction mixture was heated to 70° C., followed by a further 3 hours of stirring. Stirring was stopped and phase separation was awaited. The aqueous layer was drawn off and 540 g (6.70 mol) of fresh 50 wt. % NaOH were added, followed by a further four hours of stirring at 70° C. GC was used to show that after 4 hours the mixture consisted of di- and tri(3-pentyl)-cyclopentadiene (approximately 3:2). The products were distilled at 0.2 mbar, 51° C. and 0.2 mbar, 77° C. to 80° C., respectively. After distillation, 32 g of di and 18 g of tri(3-pentyl)cyclopentadiene were obtained. Characterization took place with the aid of GC, GC-MS, 13C- and 1H-NMR.

Provenance & Evidence