Diethyl Ether → Methyl 6-oxohexanoate

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.

1. filtrationthe reaction mixture was filtered through Florisil
2. concentrationthe filtrate was concentrated
3. distillationThe residue was distilled at reduced pressure (80–84° C. at 0.2 mmHg)

ORD record

ord-0e8fb063cff74ebcb0d4c77b40a93c43

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091357B2