Cyclopentadiene → HCID 21998290, compound

HRID 1421127Notes

Reaction equation

HRID 1421127 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 vigorously for a few minutes, then 256 g of cyclohexyl bromide (1.57 mol) were added, 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 70° C., followed by a further two hours of stirring. After two hours, stirring was stopped and phase separation was performed. The aqueous layer was drawn off and 600 g (7.5 mol) of fresh 50% strength NaOH were added, followed by a further 4 hours of stirring at 70° C. GC was used to show that the mixture comprised 10% of di- and 90% of tri(cyclohexyl)cyclopentadiene. The product was distilled at 0.04 mbar and 130° C. After distillation, 87.4 g of tri(cyclohexyl)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 L, provided with baffles, condenser, top stirrer
  3. stirringAfter one hour of stirring at room temperature
  4. temperaturethe reaction mixture was heated to 70° C.
  5. stirringof stirring
  6. waitAfter two 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. stirringof stirring at 70° C
  12. distillationThe product was distilled at 0.04 mbar and 130° C
  13. distillationAfter distillation

Sources & evidence

ORD record
ord-956b17b7e4ae45bb840d55441cab7c7d
Source dataset
uspto-grants-2000_06
Patent number
US06072067

Reaction notes

Loading…