2-Bromobutane → HCID 53842919, compound

HRID 1977527Notes

Reaction equation

HRID 1977527 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 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.

Workup

  1. customA 1 L double-walled reactor, provided with baffles, condenser, top stirrer
  2. stirringAfter half an hour of stirring at room temperature the reaction mixture
  3. stirringof stirring
  4. stirringStirring
  5. customphase separation
  6. addition400 g (5.0 mol) of fresh 50 wt. % NaOH were added
  7. waitfollowed by a further 2 hours
  8. stirringof stirring at 70° C
  9. waitto show after 2 hours
  10. additiongreater than 90% of tri(2-butyl)cyclopentadiene was 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-599478587b1f4f1eaec8f9ae32ccfac9
Source dataset
uspto-grants-2001_05
Patent number
US06232516B1

Reaction notes

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