3-Phenylbicyclo[2.2.2]octa-2,5-diene-2-carbaldehyde → 3-Phenylbicyclo[2.2.2]oct-2-ene-2-carbaldehyde

HRID 247107Notes

Reaction equation

HRID 247107 reaction equation
[CH:1]([C:3]1[CH:8]2[CH2:9][CH2:10][CH:5]([CH:6]=[CH:7]2)[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:2]>[Pd].C(OCC)(=O)C>[CH:1]([C:3]1[CH:8]2[CH2:9][CH2:10][CH:5]([CH2:6][CH2:7]2)[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:2]

Participants

4

Reactant 1

HCID 201615943-Phenylbicyclo[2.2.2]octa-2,5-diene-2-carbaldehyde

Product 1

HCID 201615933-Phenylbicyclo[2.2.2]oct-2-ene-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Formyl-2-phenylbicyclo[2,2,2]octa-2,5-diene (3.7 g; 0.018 m) 5% Palladium on charcoal (0.3 g) and ethyl acetate (100 ml) were hydrogenated for 1 week. The catalyst was filtered off and the filtrate evaporated, then the residue distilled twice; Yield 1.9 g (51%) b.p. 160° C. at 0.2 mm/Hg.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. distillationthe residue distilled twice

Sources & evidence

ORD record
ord-858c7de39a2a4677b049acbf42602d9e
Source dataset
uspto-grants-1987_11
Patent number
US04705807

Reaction notes

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