Cyclopentadiene → HCID 21998290, compound

HRID 1955392Notes

Reaction equation

HRID 1955392 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 double-walled reactor having a volume of 1 L, provided with baffles, condenser, top stirrer, thermometer and dropping funnel was charged with 600 g of clear 50% strength 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 1 hour's stirring at room temperature the reaction mixture was warmed to 70° C., followed by a further 2 hours' stirring. After 2 hours, stirring was stopped and phase separation was awaited. The water layer was drawn off and 600 g (7.5 mol) of fresh 50% strength NaOH were added, followed by a further 4 hours' stirring at 70° C. GC was used to show that at that instant 10% of di- and 90% of 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 double-walled reactor having
  2. customa volume of 1 L, provided with baffles, condenser, top stirrer
  3. stirringAfter 1 hour's stirring at room temperature the reaction mixture
  4. temperaturewas warmed to 70° C.
  5. stirring' stirring
  6. waitAfter 2 hours
  7. stirringstirring
  8. customphase separation
  9. addition600 g (7.5 mol) of fresh 50% strength NaOH were added
  10. waitfollowed by a further 4 hours
  11. stirring' stirring at 70° C
  12. distillationThe product was distilled at 0.04 mbar and 130° C
  13. distillationAfter distillation

Sources & evidence

ORD record
ord-05993f8e748443b99ed0e90a5801bbba
Source dataset
uspto-grants-2000_09
Patent number
US06124488

Reaction notes

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