Cyclopentadiene → HCID 131722566, compound

HRID 1977531Notes

Reaction equation

HRID 1977531 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].C1CC=CC=1.[OH-].[Na+].C([C:15]1[C:16]([CH2:23][CH:24]=[CH2:25])=[C:17](CC=C)[CH2:18][CH:19]=1)C=C>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH2:3]([C:16]1([CH2:23][CH:24]=[CH2:25])[CH:15]=[CH:19][CH:18]=[CH:17]1)[CH:2]=[CH2:1]

Participants

7

Reactant 4

HCID 7612CyclopentadieneHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 21998292HCID 21998292, compound

Product 1

HCID 131722566HCID 131722566, compound

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 (7.7 g, 19 mmol), allylbromide (43.6 g, 0.36 mol) and freshly cracked cyclopentadiene (11.9 g, 0.18 mol). A 50 wt. % NaOH aqueous solution (147 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 3 hours of stirring at room temperature, GC analysis showed that 6% of mono-, 75% of di- and 19% of tri(allyl)cyclopentadiene were present in the mixture. The product was distilled at reduced pressure and after vacuum distillation, 9.75 g of di(allyl)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. distillationThe product was distilled at reduced pressure
  4. distillationafter vacuum distillation

Sources & evidence

ORD record
ord-5fc9bf23c3b04f72b9717c1fa8e004b4
Source dataset
uspto-grants-2001_05
Patent number
US06232516B1

Reaction notes

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