Diethyl Ether → 4-Oxononanoic acid

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

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.