Réaction #9897

Équation de réaction

ether

Sodium acetate

PCC

→

6-oxo-hexanoic acid methyl ester

Rendement 60.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source