1,4-Methanonaphthalene → 1,2,3,4-Tetrahydro-1,4-methanonaphthalene

HRID 1614712Notes

Reaction equation

HRID 1614712 reaction equation
[C:1]12[CH2:7][C:4](=[CH:5][CH:6]=1)[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]2=1>[Pd]>[CH:4]12[CH2:7][CH:1]([CH2:6][CH2:5]1)[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]2=1

Participants

3

Reactant 1

HCID 566125711,4-Methanonaphthalene

Product 1

HCID 1382721,2,3,4-Tetrahydro-1,4-methanonaphthaleneYield 80.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4 g of a catalyst containing 10% of palladium on charcoal are added to a solution of 40 g of benzonorbornadiene in 400 cm3 of nitrogen-degassed methanol. Nitrogen is again bubbled into this mixture and the heterogeneous solution is stirred for three hours at a gauge pressure of hydrogen of 2 bars. The mixture is then filtered, concentrated under reduced pressure and benzonorbornene is purified by distillation; its boiling point at 22.5 millibars is 86° C. 33 g of a product whose nuclear magnetic resonance spectrum corresponds to the expected structure are obtained.

Workup

  1. customdegassed methanol
  2. customNitrogen is again bubbled into this mixture
  3. filtrationThe mixture is then filtered
  4. concentrationconcentrated under reduced pressure and benzonorbornene
  5. distillationis purified by distillation
  6. customis 86° C

Sources & evidence

ORD record
ord-ada69d06e6cb4efeb190d3ebb50dada3
Source dataset
uspto-grants-1993_03
Patent number
US05198567

Reaction notes

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