Cyclopentadiene → HCID 53851949, compound

HRID 1421129Notes

Reaction equation

HRID 1421129 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 double-walled reactor having a volume of 1 L, provided with baffles, condenser, top stirrer, thermometer and dropping funnel, was charged with 900 g (11.25 mol) of clear 50% strength 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 vigorously for a few minutes, then 155 g of 2-pentyl bromide (1.03 mol) were added over a period of one hour, while the reaction mixture was cooled with circulating water at 10° C. After three hours of stirring at room temperature, the reaction mixture was heated to 70° C., followed by a further two hours of stirring. Stirring was stopped and phase separation was performed. The aqueous layer was drawn off and 900 g (11.25 mol) of fresh 50% strength NaOH were added, followed by a further two hours of stirring at 70° C. GC was used to show that at that instant the mixture consisted of di- and tri(2-pentyl)cyclopentadiene in a ratio of approximately 1:1. The products were distilled at 2 mbar, 79-81° C. and 0.5 mbar, 102° C., respectively. After distillation, 28 g of di- and 40 g of tri(2-pentyl)cyclopentadiene were obtained, which were characterized with GC, GC-MS, 13C- and 1H-N MR.

Workup

  1. customA double-walled reactor having
  2. customa volume of 1 L, provided with baffles, condenser, top stirrer
  3. stirringAfter three hours of stirring at room temperature
  4. stirringof stirring
  5. stirringStirring
  6. customphase separation
  7. addition900 g (11.25 mol) of fresh 50% strength NaOH were added
  8. waitfollowed by a further two hours
  9. stirringof stirring at 70° C
  10. distillationThe products were distilled at 2 mbar, 79-81° C. and 0.5 mbar, 102° C.
  11. distillationAfter distillation, 28 g of di-

Sources & evidence

ORD record
ord-14c6ae13ca314a068056fea69d6f3c4b
Source dataset
uspto-grants-2000_06
Patent number
US06072067

Reaction notes

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