2-Bromobutane → HCID 53842919, compound

Temperature

70 °C

A double-walled reactor having a volume of 1 L, provided with baffles, condenser, top stirrer, thermometer and dropping funnel, was charged with 400 g of clear 50% strength 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 vigorously for a few minutes, then 99.8 g of 2-butyl bromide (0.73 mol) were added over a period of half an hour, while the reaction mixture was cooled with circulating water at 10° C. After half an hour's stirring at room temperature, the reaction mixture was heated to 70° C., followed by a further three hours of stirring. Stirring was stopped and phase separation was performed. The aqueous layer was drawn off and 400 g (5.0 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 more than 90% of the mixture of di-, tri- and tetra(2-butyl)cyclopentadiene was trisubstituted cyclopentadiene. The product was distilled at 1 mbar and 91° C. After distillation, 40.9 g of tri(2-butyl)cyclopentadiene were obtained, which was characterized with GC, GC-MS, 13C- and 1H-NMR.

1. customA double-walled reactor having
2. customa volume of 1 L, provided with baffles, condenser, top stirrer
3. stirringAfter half an hour's stirring at room temperature
4. stirringof stirring
5. stirringStirring
6. customphase separation
7. addition400 g (5.0 mol) of fresh 50% strength NaOH were added
8. waitfollowed by a further two hours
9. stirringof stirring at 70° C
10. distillationThe product was distilled at 1 mbar and 91° C
11. distillationAfter distillation

ORD record

ord-a77b6d960d5e445c9659b8953078f544

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06072067