Cyclopentadiene → HCID 14094221, compound

HRID 1421130Notes

Reaction equation

HRID 1421130 reaction equation
[OH-].[Na+].[CH:3]1[CH2:7][CH:6]=[CH:5][CH:4]=1.[CH2:8](Br)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH2:8]([C:4]1[CH2:3][C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:5]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 7612CyclopentadieneHCID 81401-BromooctaneHCID 14798Sodium Hydroxide

Product 1

HCID 14094221HCID 14094221, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A double-walled reactor having a volume of 1.5 L, provided with baffles, condenser, top stirrer, thermometer and dropping funnel, was charged with 900 g of clear 50% strength NaOH (11.3 mol), followed by cooling to 10° C. Then 30 g of Aliquat 336 (74 mmol) and 48 g (0.72 mol) of freshly cracked cyclopentadiene were added. The reaction mixture was stirred vigorously for a few minutes, then 577 g of octyl bromide (2.99 mol) were added over a period of one hour, while the reaction mixture was cooled with circulating water at 10° C. After one hour of stirring at room temperature, the reaction mixture was heated to 35° C., followed by a further 6 hours of stirring. Stirring was stopped and phase separation was performed. The aqueous layer was drawn off and 920 g (11.5 mol) of fresh 50% strength NaOH were added, followed by a further 5 hours of stirring at room temperature. GC was used to show that 10% of tri-, 83% of tetra- and 7% of penta(octyl)cyclopentadiene were present in the mixture. The product was distilled under reduced pressure. After vacuum distillation, 226.6 g of tetra(octyl)cyclopentadiene were obtained, which was characterized with GC, GC-MS, 13C- and 1H-NMR.

Workup

  1. customA double-walled reactor having
  2. customa volume of 1.5 L, provided with baffles, condenser, top stirrer
  3. stirringAfter one hour of stirring at room temperature
  4. temperaturethe reaction mixture was heated to 35° C.
  5. stirringof stirring
  6. stirringStirring
  7. customphase separation
  8. addition920 g (11.5 mol) of fresh 50% strength NaOH were added
  9. waitfollowed by a further 5 hours
  10. stirringof stirring at room temperature
  11. distillationThe product was distilled under reduced pressure
  12. distillationAfter vacuum distillation

Sources & evidence

ORD record
ord-aff45d2b0c5b462f895a0ee71b2abf35
Source dataset
uspto-grants-2000_06
Patent number
US06072067

Reaction notes

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