Reacción #9897

Ecuación de reacción

ether

Sodium acetate

PCC

→

6-oxo-hexanoic acid methyl ester

Rendimiento 60.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe reaction mixture was filtered through Florisil
2. 2
   Concentraciónthe filtrate was concentrated
3. 3
   workup.DISTILLATIONThe residue was distilled at reduced pressure (80–84° C. at 0.2 mmHg)

Procedimiento

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.

Fuente