2-Bromobutane → HCID 53842919, compound

HRID 1955393Notes

Reaction equation

HRID 1955393 reaction equation
[OH-].[Na+].[CH:3]1[CH2:7][CH:6]=[CH:5][CH:4]=1.[CH3:8][CH:9](Br)[CH2:10][CH3:11]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH3:8][CH:9]([C:4]1[C:3]([CH:3]([CH2:4][CH3:5])[CH3:7])=[C:7]([CH:9]([CH2:10][CH3:11])[CH3:8])[CH2:6][CH:5]=1)[CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 65542-BromobutaneHCID 7612CyclopentadieneHCID 14798Sodium Hydroxide

Product 1

HCID 53842919HCID 53842919, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

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 turbulently for a few minutes. Then 99.8 g of 2-butyl bromide (0.73 mol) were added over a period of half an hour, cooling with water taking place at the same time. After half an hour's stirring at room temperature the reaction mixture was warmed to 70° C., followed by a further three hours' stirring. Stirring was stopped and phase separation was awaited. The water layer was drawn off and 400 g (5.0 mol) of fresh 50% strength NaOH were added, followed by a further two hours' stirring at 70° C. GC was used to show that at that instant more than 90% of tri(2-butyl)cyclopentadiene were 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.

Workup

  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 the reaction mixture
  4. stirring' 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. stirring' stirring at 70° C
  10. additionwere present in the mixture of di-, tri- and tetra(2-butyl)cyclopentadiene
  11. distillationThe product was distilled at 1 mbar and 91° C
  12. distillationAfter distillation

Sources & evidence

ORD record
ord-1328809a46624cfe8a325ca0805eca64
Source dataset
uspto-grants-2000_09
Patent number
US06124488

Reaction notes

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