Ciclotic acid → Bicyclo(2.2.2)octane-1-carboxylic acid, 4-methyl-

HRID 461989Notes

Reaction equation

HRID 461989 reaction equation
[CH3:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]([OH:12])=[O:11])([CH2:6][CH2:7]1)[CH:4]=[CH:3]2.[H][H]>[Pd].C(O)C>[CH3:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]([OH:12])=[O:11])([CH2:4][CH2:3]1)[CH2:6][CH2:7]2

Participants

5

Reactant 2

HCID 21872020Ciclotic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 136544Bicyclo(2.2.2)octane-1-carboxylic acid, 4-methyl-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In this preparation a mixture containing 0.1 mole of 4-methylbicyclo[2.2.2]oct-2-ene-1-yl carboxylic acid and 1 g. of 5% palladium on carbon catalyst in 300 ml. of ethanol is stirred under hydrogen, at room temperature, until no more hydrogen is absorbed (about 2.4 liters are absorbed). The catalyst is then filtered off and the solvent removed from the filtrate by evaporation, under vacuum, affording 4-methylbicyclo[2.2.2]oct-1-yl carboxylic acid.

Workup

  1. customIn this preparation a mixture
  2. customis absorbed
  3. custom(about 2.4 liters are absorbed)
  4. filtrationThe catalyst is then filtered off
  5. customthe solvent removed from the filtrate by evaporation, under vacuum

Sources & evidence

ORD record
ord-2fd2d94ded8c4b1ea4bf2674542348a9
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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