Cyclopentadiene → HCID 21998290, 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 600 g of 50 wt. % NaOH (7.5 mol), followed by cooling to 8° C. Then 20 g of ALIQUAT 336 (49 mmol) and 33 g (0.5 mol) of freshly cracked cyclopentadiene were added. The reaction mixture was stirred turbulently for a few minutes. Then 256 g of cyclohexyl bromide (1.57 mol) were added, cooling with water taking place at the same time. After stirring for 1 hour at room temperature the reaction mixture was heated and stirred at 70° C. for 2 hours. After 2 hours the mixture was allowed to cool to room temperature and then phases were separated. The aqueous layer was drawn off and 600 g (7.5 mol) of fresh 50 wt. % NaOH were added, followed by further stirring for 4 hours at 70° C. GC was used to show that after 4 hours 10% di- and 90% tri(cyclohexyl)-cyclopentadiene were present in the mixture. The product was distilled at 0.04 mbar and 130° C. After distillation, 87.4 g of tri(cyclohexyl)cyclopentadiene were obtained. Characterization took place with the aid of GC, GC-MS, 13C and 1H-NMR.

Provenance & Evidence