Cyclopentadiene → HCID 21998290, compound

HRID 1977526Notes

Reaction equation

HRID 1977526 reaction equation
[OH-].[Na+].[CH:3]1[CH2:7][CH:6]=[CH:5][CH:4]=1.[CH:8]1(Br)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH:8]1([C:4]2[C:3]([CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[C:7]([CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH2:6][CH:5]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 7612CyclopentadieneHCID 7960Cyclohexyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 21998290HCID 21998290, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
8 °C

Procedure

A 1 L double-walled reactor, provided with baffles, condenser, top stirrer, thermometer and dropping funnel was charged with 600 g of 50 wt. % NaOH (7.5 mol), followed by cooling to 8° C. Then 20 g of ALIQUAT 336 (49 mmol) and 33 g (0.5 mol) of freshly cracked cyclopentadiene were added. The reaction mixture was stirred turbulently for a few minutes. Then 256 g of cyclohexyl bromide (1.57 mol) were added, cooling with water taking place at the same time. After stirring for 1 hour at room temperature the reaction mixture was heated and stirred at 70° C. for 2 hours. After 2 hours the mixture was allowed to cool to room temperature and then phases were separated. The aqueous layer was drawn off and 600 g (7.5 mol) of fresh 50 wt. % NaOH were added, followed by further stirring for 4 hours at 70° C. GC was used to show that after 4 hours 10% di- and 90% tri(cyclohexyl)-cyclopentadiene were present in the mixture. The product was distilled at 0.04 mbar and 130° C. After distillation, 87.4 g of tri(cyclohexyl)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 stirring for 1 hour at room temperature the reaction mixture
  3. temperaturewas heated
  4. stirringstirred at 70° C. for 2 hours
  5. temperatureto cool to room temperature
  6. customphases were separated
  7. addition600 g (7.5 mol) of fresh 50 wt. % NaOH were added
  8. stirringby further stirring for 4 hours at 70° C
  9. customafter 4 hours
  10. distillationThe product was distilled at 0.04 mbar and 130° C
  11. distillationAfter distillation

Sources & evidence

ORD record
ord-b705686d33204dd0b3a1d61c85373b07
Source dataset
uspto-grants-2001_05
Patent number
US06232516B1

Reaction notes

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