Hydroquinone → 2-Norbornanecarbonitrile

HRID 1575997Notes

Reaction equation

HRID 1575997 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[C:5]1([CH:12]=[CH:11][C:9](O)=CC=1)O.[CH:13]1CC=CC=1>C1C=CC=CC=1>[C:1]([CH:2]1[CH2:13][CH:12]2[CH2:5][CH:3]1[CH2:9][CH2:11]2)#[N:4]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 7612CyclopentadieneHCID 7855Acrylonitrile

Product 1

HCID 1022312-Norbornanecarbonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

159 g (3 moles) of acrylonitrile were dissolved in 100 ml of benzene and warmed to 50°C. after adding a pinch of hydroquinone. 196 g (3 moles) of cyclopentadiene were added dropwise at this temperature, with intensive stirring. In the course thereof, the temperature of the reaction mixture rose (it should not exceed 70°C.). After the exothermic reaction had subsided, the mixture was stirred for 1 hour at 80°C. The solvent was then distilled off and the residue was rectified in vacuo. This gave 272 g (76% of theory) of 2-cyano-bicyclo[2,2,1]heptene-5 of boiling point 82°-87°C/15 mm Hg.

Workup

  1. customexceed 70°C.
  2. customAfter the exothermic reaction
  3. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-2969b5ff0caf427d95d1af8194978c5b
Source dataset
uspto-grants-1976_09
Patent number
US03979204

Reaction notes

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