3-Phenylbicyclo[2.2.2]octa-2,5-diene-2-carbaldehyde → 3-Phenylbicyclo[2.2.2]oct-2-ene-2-carbaldehyde
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
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe catalyst was filtered off
- customthe filtrate evaporated
- 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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