Benzyl Bromide → HCID 131722569, compound

HRID 1977534Notes

Reaction equation

HRID 1977534 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH2:1]([C:10]1([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=[CH:13][CH:12]=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 7612CyclopentadieneHCID 14798Sodium Hydroxide

Product 1

HCID 131722569HCID 131722569, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
40 °C

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 (8.1 g, 20 mmol), benzylbromide (62.9 g, 0.37 mol) and freshly cracked cyclopentadiene (11.9 g, 0.18 mol). A 50 wt. % NaOH aqueous solution (149 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 0.5 hour, the reaction mixture was heated 40° C. After 4 hours, stirring was stopped and the phases separated, the aqueous basic solution was isolated, removed and replaced with a fresh 50 wt. % NaOH solution (146 g). After 0.5 hours of stirring at 40° C., the stirring was stopped, the layers separated and the product was distilled at reduced pressure. After vacuum distillation, 45.0 g of di-(benzyl)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. waitAfter 4 hours
  4. customthe phases separated
  5. customthe aqueous basic solution was isolated
  6. customremoved
  7. stirringAfter 0.5 hours of stirring at 40° C.
  8. customthe layers separated
  9. distillationthe product was distilled at reduced pressure
  10. distillationAfter vacuum distillation

Sources & evidence

ORD record
ord-20ee6f0239954a2baab13214f0016c6e
Source dataset
uspto-grants-2001_05
Patent number
US06232516B1

Reaction notes

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