Ammonia → 3-Methylheptanoic acid

HRID 461984Notes

Reaction equation

HRID 461984 reaction equation
[OH-:1].[K+].CCCCCC.[CH3:9][CH:10]([CH2:15][C:16](N)=[O:17])[CH2:11][CH2:12][CH2:13][CH3:14].N>C(O)C>[CH3:9][CH:10]([CH2:15][C:16]([OH:17])=[O:1])[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8058HexaneHCID 14797Potassium HydroxideHCID 21809237Hex-2-yl acetamide

Product 1

HCID 52826833-Methylheptanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In this preparation 2 ml. of 30% aqueous potassium hydroxide is admixed with 0.1 mole of exobicyclo[3.1.0]hex-2-yl acetamide in 20 ml. of ethanol and warmed to 70° C and stirred at this temperature until no more ammonia evolves. The ethanol solvent is then removed by evaporation under vacuum and the residue poured into 100 ml. of water and extracted three times with ethyl ether. The aqueous solution is acidified to about pH 2 with 5N aqueous hydrochloric acid and then extracted three times with ethyl ether. The ethyl ether extracts are combined and dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under vacuum to remove the ethyl ether, affording exobicyclo[3.1.0]hex-2-yl acetic acid as a residue.

Workup

  1. customIn this preparation 2 ml
  2. customThe ethanol solvent is then removed by evaporation under vacuum
  3. additionthe residue poured into 100 ml
  4. extractionof water and extracted three times with ethyl ether
  5. extractionextracted three times with ethyl ether
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate evaporated under vacuum
  9. customto remove the ethyl ether

Sources & evidence

ORD record
ord-b0f70c6380b84ac3894df8b5f1c99067
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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