Ethanol → (Bicyclo[2.2.1]heptan-7-yl)acetic acid

HRID 461986

Reaction equation

HRID 461986 reaction equation
[C:1]([CH:6]=[C:7]1[CH:11]2[CH2:12][CH2:13][CH:8]1[CH2:9][CH2:10]2)([O:3]CC)=[O:2].C(O)C.[H][H].[OH-].[K+]>[Pd].O>[CH:8]12[CH:7]([CH2:6][C:1]([OH:3])=[O:2])[CH:11]([CH2:10][CH2:9]1)[CH2:12][CH2:13]2

Participants

7

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 213926737-Carbethoxymethylene-bicyclo[2.2.1]heptaneHCID 178418361HCID 178418361, compound

Product 1

HCID 21392682(Bicyclo[2.2.1]heptan-7-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture containing 0.05 mole of 7-carbethoxymethylene-bicyclo[2.2.1]heptane and 5 g. of 5% palladium on carbon catalyst and 250 ml. of ethanol is stirred under hydrogen until no more hydrogen is absorbed (about 1.2 liters are absorbed). The catalyst is removed by filtration and a solution containing 0.1 mole of potassium hydroxide in 20 ml. of water is added to the filtrate. The solution is then refluxed until no more starting material is observed by thin-layer chromatographic monitoring. The solvent is then removed by evaporation under vacuum and the resulting residue dissolved in 200 ml. of water and extracted three times with ethyl ether. The remaining aqueous phase is acidified with dilute aqueous hydrochloric acid and then extracted three times with ethyl acetate. The combined organic extracts are washed with water, then dried with anhydrous magnesium sulfate and filtered. The filtrate is evaporated to dryness, under vacuum, affording bicyclo[2.2.1]hept-7-yl acetic acid.

Workup

  1. customis absorbed
  2. custom(about 1.2 liters are absorbed)
  3. customThe catalyst is removed by filtration
  4. temperatureThe solution is then refluxed until
  5. customThe solvent is then removed by evaporation under vacuum
  6. dissolutionthe resulting residue dissolved in 200 ml
  7. extractionof water and extracted three times with ethyl ether
  8. extractionextracted three times with ethyl acetate
  9. washThe combined organic extracts are washed with water
  10. dry with materialdried with anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customThe filtrate is evaporated to dryness, under vacuum

Sources & evidence

ORD record
ord-71f4d2c2c39e4eafae64175a289cffc3
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Linked notes

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