2-Bromobutane → HCID 53842919, 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 400 g of 50 wt. % NaOH (5 mol). Then 9.6 g of ALIQUAT 336 (24 mmol) and 15.2 g (0.23 mol) of freshly cracked cyclopentadiene were added. The reaction mixture was stirred turbulently for a few minutes. Then 99.8 g of 2-butyl bromide (0.73 mol) were added in half an hour, cooling with water taking place at the same time. After half an 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 400 g (5.0 mol) of fresh 50 wt. % NaOH were added, followed by a further 2 hours of stirring at 70° C. GC was used to show after 2 hours greater than 90% of tri(2-butyl)cyclopentadiene was present in the mixture of di, tri- and tetra(2-butyl)cyclopentadiene. The product was distilled at 1 mbar and 91° C. After distillation, 40.9 g of tri(2-butyl)cyclopentadiene were obtained. Characterization took place with the aid of GC, GC-MS, 13C- and 1H-NMR.

Provenance & Evidence