5-(Bicyclo[3.2.1]oct-2-ylidene)pentanoic acid → 5-(Bicyclo[3.2.1]oct-2-yl)pentanoic acid

HRID 26306Notes

Reaction equation

HRID 26306 reaction equation
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][C:2]2=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[H][H]>C(O)C.[Pt]=O>[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH:2]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 538784935-(Bicyclo[3.2.1]oct-2-ylidene)pentanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 213254325-(Bicyclo[3.2.1]oct-2-yl)pentanoic acid

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 3.4 g (16.3 mmol) of 5-(bicyclo[3.2.1]-oct-2-ylidene)pentanoic acid in 100 ml of absolute ethanol was hydogenated at 50 psi over 300 mg of platinum oxide in a Parr apparatus. After 1.5 hr hydrogen uptake became slow. Afer 4 hr the system was flushed with nitrogen, and the catalyst was removed by filtration through diatomaceous earth filter aid (Celite). The filtrate was evaporated in vacuo to yield 3.25 g (96%) of quite pure 5-(bicyclo[3.2.1]oct-2-yl)pentanoic acid as a colorless oil.

Workup

  1. customAfer 4 hr the system was flushed with nitrogen
  2. customthe catalyst was removed by filtration through diatomaceous earth
  3. filtrationfilter aid (Celite)
  4. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-61d4223eb17a4a3f9e8ba505962f1c91
Source dataset
uspto-grants-1979_04
Patent number
US04149017

Reaction notes

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