1,3-Cyclohexadiene → 3-(3,4-Dichlorophenyl)bicyclo[2.2.2]oct-5-ene-2-carbonitrile

HRID 1576379Notes

Reaction equation

HRID 1576379 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])/[CH:5]=[CH:6]/[C:7]#[N:8].[CH:13]1[CH2:18][CH2:17][CH:16]=[CH:15][CH:14]=1>>[C:7]([CH:6]1[CH:5]([C:4]2[CH:9]=[CH:10][C:11]([Cl:12])=[C:2]([Cl:1])[CH:3]=2)[CH:15]2[CH2:16][CH2:17][CH:18]1[CH:13]=[CH:14]2)#[N:8]

Participants

3

Reactant 2

HCID 116051,3-CyclohexadieneHCID 10465325HCID 10465325, compound

Product 1

HCID 201616473-(3,4-Dichlorophenyl)bicyclo[2.2.2]oct-5-ene-2-carbonitrile

Procedure

trans-3,4-Dichlorocinnamonitrile (20 g.) and cyclohexadiene (16 g.) were heated at 150°C. for 3 weeks. The solution was evaporated, the resultant oil purified by column chromatography and crystallised from methanol to yield white crystals of 5-cyano-6-(3',4'-dichlorophenyl)bicyclo[2,2,2]oct-2-ene. The latter (14 g.) was hydrogenated as described in Example 1 to yield trans-3-cyano-2-(3',4'-dichlorophenyl)bicyclo[2,2,2]octane as white crystals (14 g.). Similarly the following compounds were prepared:

Workup

  1. customThe solution was evaporated
  2. customthe resultant oil purified by column chromatography
  3. customcrystallised from methanol

Sources & evidence

ORD record
ord-d05043cd0c0f432d85bdb566d42530c7
Source dataset
uspto-grants-1976_09
Patent number
US03980785

Reaction notes

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