Dicyclopentadiene → 5-Phenylbicyclo[2.2.1]hept-2-ene

HRID 1597440Notes

Reaction equation

HRID 1597440 reaction equation
[CH2:1]1[CH:5]2[CH:6]3[CH:10]=[CH:9][CH:8]([CH:4]2[CH:3]=[CH:2]1)[CH2:7]3.[CH2:11]=[CH:12][C:13]1C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]1([CH:5]2[CH2:4][CH:8]3[CH2:7][CH:6]2[CH:10]=[CH:9]3)[CH:2]=[CH:3][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6492DicyclopentadieneHCID 7501Styrene

Product 1

HCID 1386745-Phenylbicyclo[2.2.1]hept-2-ene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

Dicyclopentadiene (180 g), styrene (140 g), toluene (36 g), and N,N-diethylbydroxylamine (0.35 g) (added as a polymerization inhibitor) were added to a stainless steel reactor. The mixture was heated to 150° C. for 6 hours. The low boiling fraction was removed from the resulting reaction mixture on the roto-vap. The remaining higher boiling fraction was fractionally distilled. The fraction distilling at 130° C. @ 4 mm Hg was analyzed by GC and found to be 96% 5-phenylnorbornene.

Workup

  1. additionwere added to a stainless steel reactor
  2. customThe low boiling fraction was removed from the resulting reaction mixture on the roto-vap
  3. distillationThe remaining higher boiling fraction was fractionally distilled
  4. distillationThe fraction distilling at 130° C.

Sources & evidence

ORD record
ord-acb3882feeb0458e957dc131daefdc85
Source dataset
uspto-grants-2001_09
Patent number
US06294616B1

Reaction notes

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