Diethyl Ether → Methyl 6-oxohexanoate

Participants

Reaction Steps

The foregoing crude product was dissolved in CH2Cl2 (300 mL). Sodium acetate (2.6 g, 32 mmol) and PCC (32.7 g, 50 mmol) was added. After being stirred at room temperature for 2 h, ether (2000 mL) was added, the reaction mixture was filtered through Florisil, and the filtrate was concentrated. The residue was distilled at reduced pressure (80–84° C. at 0.2 mmHg) to give 6-oxo-hexanoic acid methyl ester (8.58 g, 60%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 9.72 (1H, t, J=1.5 Hz), 3.62 (3H, s), 2.43 (2H, m), 2.29 (2H, m), 1.62 (4H, m); 13C NMR (75 MHz, CDCl3) δ 201.99, 173.64, 51.73, 43.66, 33.88, 24.53, 21.69.

Provenance & Evidence