Cyclopentadiene → HCID 14094221, compound

HRID 1977530Notes

Reaction equation

HRID 1977530 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 1.5 L double-walled reactor, provided with baffles, condenser, top stirrer, thermometer and dropping funnel was charged with 900 g of 50 wt. % 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, cooling with water taking place at the same time. After 1 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 awaited. The aqueous layer was drawn off and 920 g (11.5 mol) of fresh 50 wt. % NaOH were added, followed by a further 5 hours of stirring at room temperature. GC was used to show that after 5 hours 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 1.5 L double-walled reactor, provided with baffles, condenser, top stirrer
  2. stirringAfter 1 hour of stirring at room temperature the reaction mixture
  3. temperaturewas heated to 35° C.
  4. stirringof stirring
  5. stirringStirring
  6. customphase separation
  7. addition920 g (11.5 mol) of fresh 50 wt. % NaOH were added
  8. waitfollowed by a further 5 hours
  9. stirringof stirring at room temperature
  10. customafter 5 hours
  11. distillationThe product was distilled at reduced pressure
  12. distillationAfter vacuum distillation

Sources & evidence

ORD record
ord-bd7d8f254fb241bba0ff12fde51a34d1
Source dataset
uspto-grants-2001_05
Patent number
US06232516B1

Reaction notes

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