Synthesis
General Procedure: A potassium solution is obtained by contacting a potassium microscope with a THF (0.2 mol/L) solution of 18-crown-6 at -20 °C. An appropriate amount of ketone (THF solution, 1 mol/L) is added dropwise to the resulting blue potassium solution ([K-] = 0.22 mol/L) until the color changes. The obtained cycloalkanone ester and acrylate are then alkylated or acylated. For this purpose, iodomethane or acetyl chloride is added to the enolate under argon atmosphere. The reaction is carried out at room temperature for 60 minutes. The formed potassium halide is separated by filtration. The reaction products are then isolated and analyzed using conventional preparative methods.
All compounds obtained had a purity > 96% (GC), and appropriate spectroscopic and analytical data are provided. 2-Acetylcyclopentanone, yield 32%.
Chemical Properties
clear light yellow to brown liquid
Uses
2-Acetylcyclopentanone was used to evaluate the protective abilities of 2-ACP in a mouse model of acetaminophen (APAP) hepatotoxicity.
Purification Methods
Dissolve the ketone in pet ether (b 30-60o), wash it with saturated aqueous NaHCO3, dry over Drierite and fractionate in a vacuum. It gives a violet colour with ethanolic FeCl3 and is only slowly hydrolysed by 10% aqueous KOH but rapidly on boiling to yield 6-oxoheptanoic acid. [Manyik et al. J Am Chem Soc 75 5030 1953, Acheson J Chem Soc 4232 1956, UV: Martin & Frenelius J Am Chem Soc 81 2342 1959.] It gives a gray green Cu salt from Et2O/pentane, m 237-238o [House & Wasson J Am Chem Soc 79 1488 1957].
