Cyclopentadiene → HCID 53851949, compound

HRID 1977528Notes

Reaction equation

HRID 1977528 reaction equation
[OH-].[Na+].[CH:3]1[CH2:7][CH:6]=[CH:5][CH:4]=1.[CH3:8][CH:9](Br)[CH2:10][CH2:11][CH3:12]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH3:8][CH:9]([C:4]1[C:3]([CH:4]([CH2:3][CH2:7][CH3:6])[CH3:5])=[C:7]([CH:9]([CH2:10][CH2:11][CH3:12])[CH3:8])[CH2:6][CH:5]=1)[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 7612CyclopentadieneHCID 78902-BromopentaneHCID 14798Sodium Hydroxide

Product 1

HCID 53851949HCID 53851949, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A 1 L double-walled reactor, provided with baffles, condenser, top stirrer, thermometer and dropping funnel was charged with 900 g (11.25 mol) of 50 wt. % NaOH. Then 31 g of ALIQUAT 336 (77 mmol) and 26.8 g (0.41 mol) of freshly cracked cyclopentadiene were added. The reaction mixture was stirred turbulently for a few minutes. Then 155 g of 2-pentyl bromide (1.03 mol) were added over a period of 1 hour, cooling with water taking place at the same time. After 3 hours of stirring at room temperature the reaction mixture was heated to 70° C., followed by a further 2 hours of stirring. Stirring was stopped and phase separation was awaited. The aqueous layer was drawn off and 900 g (11.25 mol) of fresh 50 wt. % NaOH were added, followed by a further two hours of stirring at 70° C. GC was used to show that after 2 hours the mixture consisted of di- and tri(2-pentyl)cyclopentadiene (approximately 1:1). The products were distilled at 2 mbar, 79° C. to 81° C. and 0.5 mbar, 102° C., respectively. After distillation, 28 g of di- and 40 g of tri(2-pentyl)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 3 hours of stirring at room temperature the reaction mixture
  3. stirringof stirring
  4. stirringStirring
  5. customphase separation
  6. addition900 g (11.25 mol) of fresh 50 wt. % NaOH were added
  7. waitfollowed by a further two hours
  8. stirringof stirring at 70° C
  9. customafter 2 hours
  10. distillationThe products were distilled at 2 mbar, 79° C. to 81° C. and 0.5 mbar, 102° C.
  11. distillationAfter distillation, 28 g of di-

Sources & evidence

ORD record
ord-d9530c4ebe7b47b3b61e36047263f7ad
Source dataset
uspto-grants-2001_05
Patent number
US06232516B1

Reaction notes

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