Cyclopentadiene → HCID 131722568, compound

HRID 1977533Notes

Reaction equation

HRID 1977533 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.[CH:8]1[CH2:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH:7]1([C:9]2([CH:6]3[CH2:5][CH2:4][CH:3]=[CH:2][CH2:7]3)[CH:8]=[CH:12][CH:11]=[CH:10]2)[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

6

Reactant 3

HCID 7612CyclopentadieneHCID 14798Sodium HydroxideHCID 1370573-Bromocyclohexene

Product 1

HCID 131722568HCID 131722568, compoundYield 88.4%

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 (7.6 g, 19 mmol), 3-bromocyclohexene (58.8 g, 0.37 mol) and freshly cracked cyclopentadiene (11.9 g, 0.18 mol). A 50 wt. % NaOH aqueous solution (152 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 4 hours of stirring at room temperature, stirring was stopped and the phases separated, the aqueous basic solution was isolated and removed. GC analysis showed that 4 % of mono- and 96% of di-(3-cyclohexenyl)cyclopentadiene were present in the mixture. The product was distilled at reduced pressure and after vacuum distillation, 36.0 g of di-(3-cyclohexenyl)cyclopentadiene were obtained. Characterization 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. customturbulently stirred reaction mixture
  4. stirringstirring
  5. customthe phases separated
  6. customthe aqueous basic solution was isolated
  7. customremoved
  8. distillationThe product was distilled at reduced pressure
  9. distillationafter vacuum distillation

Sources & evidence

ORD record
ord-041472637af74988884b88125935dbbb
Source dataset
uspto-grants-2001_05
Patent number
US06232516B1

Reaction notes

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