Cyclopentadiene → HCID 53827973, compound

HRID 1977529Notes

Reaction equation

HRID 1977529 reaction equation
[OH-].[Na+].[CH:3]1[CH2:7][CH:6]=[CH:5][CH:4]=1.[CH3:8][CH2:9][CH:10](Br)[CH2:11][CH3:12]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH3:8][CH2:9][CH:10]([C:4]1[C:3]([CH:3]([CH2:7][CH3:6])[CH2:4][CH3:5])=[C:7]([CH:10]([CH2:11][CH3:12])[CH2:9][CH3:8])[CH2:6][CH:5]=1)[CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 7612CyclopentadieneHCID 14798Sodium HydroxideHCID 157383-Bromopentane

Product 1

HCID 53827973HCID 53827973, 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 430 g (5.4 mol) of 50 wt. % NaOH. Then 23 g of ALIQUAT 336 (57 mmol) and 27 g (0.41 mol) of freshly cracked cyclopentadiene were added. The reaction mixture was stirred turbulently for a few minutes. Then 150 g of 3-pentyl bromide (1.0 mol) were added over a period of 1 hour, cooling with water taking place at the same time. After 1 hour of stirring at room temperature the reaction mixture was heated to 70° C., followed by a further 3 hours of stirring. Stirring was stopped and phase separation was awaited. The aqueous layer was drawn off and 540 g (6.70 mol) of fresh 50 wt. % NaOH were added, followed by a further four hours of stirring at 70° C. GC was used to show that after 4 hours the mixture consisted of di- and tri(3-pentyl)-cyclopentadiene (approximately 3:2). The products were distilled at 0.2 mbar, 51° C. and 0.2 mbar, 77° C. to 80° C., respectively. After distillation, 32 g of di and 18 g of tri(3-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 1 hour of stirring at room temperature the reaction mixture
  3. stirringof stirring
  4. stirringStirring
  5. customphase separation
  6. addition540 g (6.70 mol) of fresh 50 wt. % NaOH were added
  7. waitfollowed by a further four hours
  8. stirringof stirring at 70° C
  9. customafter 4 hours
  10. distillationThe products were distilled at 0.2 mbar, 51° C. and 0.2 mbar, 77° C. to 80° C.
  11. distillationAfter distillation, 32 g of di

Sources & evidence

ORD record
ord-c8841da686b149eab79ca2076c5f6c62
Source dataset
uspto-grants-2001_05
Patent number
US06232516B1

Reaction notes

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