Dicyclopentadiene → Butyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

HRID 2194319Notes

Reaction equation

HRID 2194319 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH:2]=[CH2:3].C1CC=CC=1.[CH2:15]1[CH:19]2[CH:20]3C=CC([CH:18]2C=[CH:16]1)C3>>[CH2:6]([O:5][C:1]([CH:2]1[CH2:18][CH:19]2[CH2:20][CH:3]1[CH:16]=[CH:15]2)=[O:4])[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 3

HCID 6492DicyclopentadieneHCID 7612CyclopentadieneHCID 8846Butyl Acrylate

Product 1

HCID 15608148Butyl bicyclo[2.2.1]hept-5-ene-2-carboxylateYield 93%

Procedure

A mixture of butyl acrylate (41.62 g, 0.032 mol) and cyclopentadiene (31.76 g, 0.48 mol, freshly prepared from dicyclopentadiene) was stirred in a flask with cooling in a cold water bath. After 1 hour, the mixture was stirred at 55° C. for 30 minutes. The mixture was then distilled under reduced pressure (60-65° C. @0.4 mmHg) to give the product as a colorless oil (yield 70.29 g, 93%).

Workup

  1. temperaturewith cooling in a cold water bath
  2. stirringthe mixture was stirred at 55° C. for 30 minutes
  3. distillationThe mixture was then distilled under reduced pressure (60-65° C. @0.4 mmHg)

Sources & evidence

ORD record
ord-1ee78da212ca4486b307a6451ca40483
Source dataset
uspto-grants-2012_12
Patent number
US08333360B2

Reaction notes

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