Dicyclopentadiene → HCID 68574788, compound

HRID 1049950Notes

Reaction equation

HRID 1049950 reaction equation
[C:1]([O:4][CH2:5]C=C)(=[O:3])[CH3:2].C1[CH:12]2[CH:13]3[CH:17]=[CH:16][CH:15]([CH:11]2C=C1)[CH2:14]3>>[CH3:5][O:4][C:1](=[O:3])[CH3:2].[CH:13]12[CH2:14][CH:15]([CH2:16][CH2:17]1)[CH:11]=[CH:12]2

Participants

3

Reactant 2

HCID 6492DicyclopentadieneHCID 11584Allyl acetate

Product 1

HCID 68574788HCID 68574788, compound

Conditions

Temperature
220 °C

Procedure

Into a suitable high pressure tube reactor were placed allyl acetate and dicyclopentadiene (DCPD) at 4:1 molar ratio based on cyclopentadiene monomer, and heated in a hot oil bath maintained at 220° C., and maintained at that temperature for four hours. At the end of the reaction, the high pressure tube was removed from the bath and quenched in a wet ice bath. The tube was washed then with methanol and dichloromethane and weighed to verify that no leakage had occurred. The resultant crude monomer sample was analyzed by GC-MS, which showed about 7.5% unreacted allyl acetate, 10% exo-/endo-norbornene methanol, 82% exo-/endo-norbornene methyl acetate and 0.6% (1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalen-2-yl)methanol. Fractional distillation of the crude mixture resulted in the isolation of norbornene methyl acetate of greater than >99.6% purity.

Workup

  1. customInto a suitable high pressure tube reactor were placed
  2. temperatureheated in a hot oil bath
  3. temperaturemaintained at that temperature for four hours
  4. customAt the end of the reaction
  5. customthe high pressure tube was removed from the bath
  6. customquenched in a wet ice bath
  7. washThe tube was washed
  8. distillationFractional distillation of the crude mixture

Sources & evidence

ORD record
ord-da6df11a269649f5b0b7f334dbb3eef0
Source dataset
uspto-grants-2016_07
Patent number
US09382271B2

Reaction notes

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