Cyclopentadiene → HCID 53851949, compound

Participants

Reaction Conditions

Reaction Steps

A double-walled reactor having a volume of 1 L, provided with baffles, condenser, top stirrer, thermometer and dropping funnel, was charged with 900 g (11.25 mol) of clear 50% strength 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 vigorously for a few minutes, then 155 g of 2-pentyl bromide (1.03 mol) were added over a period of one hour, while the reaction mixture was cooled with circulating water at 10° C. After three hours of stirring at room temperature, the reaction mixture was heated to 70° C., followed by a further two hours of stirring. Stirring was stopped and phase separation was performed. The aqueous layer was drawn off and 900 g (11.25 mol) of fresh 50% strength NaOH were added, followed by a further two hours of stirring at 70° C. GC was used to show that at that instant the mixture consisted of di- and tri(2-pentyl)cyclopentadiene in a ratio of approximately 1:1. The products were distilled at 2 mbar, 79-81° C. and 0.5 mbar, 102° C., respectively. After distillation, 28 g of di- and 40 g of tri(2-pentyl)cyclopentadiene were obtained, which were characterized with GC, GC-MS, 13C- and 1H-N MR.

Provenance & Evidence