Cyclopentadiene → HCID 14094221, compound

HRID 1953374Notes

Reaction equation

HRID 1953374 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 turbulently for a few minutes. Then 577 g of octyl bromide (2.99 mol) were added in one hour's time, cooling with water taking place at the same time. After 1 hour's stirring at room temperature the reaction mixture was heated to 35° C., followed by a further 6 hours' stirring. Stirring was stopped and phase separation was awaited. The water layer was drawn off and 920 g (11.5 mol) of fresh 50% strength NaOH were added, followed by a further 5 hours' stirring at room temperature. GC was used to show that at that instant 10% of tri-, 83% of tetra- and 7% of penta(octyl)cyclopentadiene were present in the mixture. The product was distilled at reduced pressure. After vacuum distillation, 226.6 g of tetra(octyl)cyclopentadiene were obtained. Characterization of the product took place with the aid of GC, GC-MS, 13C- and 1H-NMR.

Workup

  1. customA double-walled reactor having
  2. customa volume of 1.5 L, provided with baffles, condenser, top stirrer
  3. stirringAfter 1 hour's stirring at room temperature the reaction mixture
  4. temperaturewas heated to 35° C.
  5. stirring' 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. stirring' stirring at room temperature
  11. distillationThe product was distilled at reduced pressure
  12. distillationAfter vacuum distillation

Sources & evidence

ORD record
ord-7d212898f1fd439082bb3cb461a580ce
Source dataset
uspto-grants-2000_09
Patent number
US06117811

Reaction notes

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