Cyclopentadiene → HCID 53851949, 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 900 g (11.25 mol) of 50 wt. % NaOH. Then 31 g of ALIQUAT 336 (77 mmol) and 26.8 g (0.41 mol) of freshly cracked cyclopentadiene were added. The reaction mixture was stirred turbulently for a few minutes. Then 155 g of 2-pentyl bromide (1.03 mol) were added over a period of 1 hour, cooling with water taking place at the same time. After 3 hours of stirring at room temperature the reaction mixture was heated to 70° C., followed by a further 2 hours of stirring. Stirring was stopped and phase separation was awaited. The aqueous layer was drawn off and 900 g (11.25 mol) of fresh 50 wt. % NaOH were added, followed by a further two hours of stirring at 70° C. GC was used to show that after 2 hours the mixture consisted of di- and tri(2-pentyl)cyclopentadiene (approximately 1:1). The products were distilled at 2 mbar, 79° C. to 81° C. and 0.5 mbar, 102° C., respectively. After distillation, 28 g of di- and 40 g of tri(2-pentyl)cyclopentadiene were obtained. Characterization took place with the aid of GC, GC-MS, 13C- and 1H-NMR.

Provenance & Evidence