Cyclopentadiene → HCID 131722567, compound

HRID 1977532Notes

Reaction equation

HRID 1977532 reaction equation
Br[CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5].[CH:7]1[CH2:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH3:5][C:4]([CH3:6])=[CH:3][CH2:2][C:8]1([CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5])[CH:7]=[CH:11][CH:10]=[CH:9]1

Participants

6

Reactant 3

HCID 7612CyclopentadieneHCID 14798Sodium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 131722567HCID 131722567, compoundYield 16.8%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A 1.0 L double-walled reactor, provided with baffles, condenser, top stirrer, thermometer and dropping funnel equipped with a nitrogen inlet was charged with ALIQUAT 336 (4.0 g, 10 mmol), 4-bromo-2-methyl-2-butene (30.0 g, 0.20 mol) and freshly cracked cyclopentadiene (6.6 g, 0.10 mol). A 50 wt. % NaOH aqueous solution (84 g) was then added via the dropping funnel to the turbulently stirred reaction mixture. The reaction mixture was cooled with water during the addition of the base. After 5.5 hours of stirring at room temperature, the stirring was stopped, the layers separated and the product was distilled at reduced pressure. After vacuum distillation, 3.4 g of di-(3-methyl-2-butenyl)-cyclopentadiene were obtained. Characterizaton of the product took place with the aid of GC, GC-MS, 13C- and 1H-NMR.

Workup

  1. customA 1.0 L double-walled reactor, provided with baffles, condenser, top stirrer
  2. customequipped with a nitrogen inlet
  3. customthe layers separated
  4. distillationthe product was distilled at reduced pressure
  5. distillationAfter vacuum distillation

Sources & evidence

ORD record
ord-642115a33575436a914a98037c739b60
Source dataset
uspto-grants-2001_05
Patent number
US06232516B1

Reaction notes

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