Diethyl Ether → 4-Oxopelargonic acid

HRID 980850Notes

Reaction equation

HRID 980850 reaction equation
C([C:3]([C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])([CH2:7][C:8]([O-:10])=[O:9])C([O-])=O)C.[OH-].[Na+].CCOCC>O>[O:17]=[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 86741240HCID 86741240, compound

Product 1

HCID 224334-Oxopelargonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The part (a) ester (1.0 g, 3.7 mmol) was treated with a solution of NaOH (1.5 g, 37.5 mmol) in water (15 ml). The heterogeneous mixture was heated under gentle reflux for 9 hours. After cooling, ether (20 ml) was added. The layers were separated. The aqueous layer was washed with ether (10 ml) and then acidified to pH 2 using concentrated HCl. The product was extracted into ether (3×20 ml). The ether extracts were washed with saturated NaCl solution, dried (MgSO4), and freed of solvent in vacuo leaving an oil which gradually solidified (345 mg). This was crystallized from petroleum ether to give title acid (189.9 mg, 30%) as colorless needles, m.p. 64°-66° C.

Workup

  1. temperatureThe heterogeneous mixture was heated
  2. temperatureunder gentle reflux for 9 hours
  3. temperatureAfter cooling
  4. customThe layers were separated
  5. washThe aqueous layer was washed with ether (10 ml)
  6. extractionThe product was extracted into ether (3×20 ml)
  7. washThe ether extracts were washed with saturated NaCl solution
  8. dry with materialdried (MgSO4)
  9. customleaving an oil which
  10. customThis was crystallized from petroleum ether
  11. customto give title acid (189.9 mg, 30%) as colorless needles, m.p. 64°-66° C.

Sources & evidence

ORD record
ord-782f3ebb4859429aacd771c6c0ca58ef
Source dataset
uspto-grants-1987_01
Patent number
US04639461

Reaction notes

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