Acetic Acid → Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Participants

Reaction Conditions

Reaction Steps

21.7 g (0.72 mol) of sodium hydride (80% strength, 20% mineral oil) are weighed into a liter of diethyl ether p.a. and 85.5 g (127 ml, 0.72 mol) of diethyl carbonate (VK 22-010) are subsequently added. A solution of 100 g (0.72 mol) of 4-fluoroacetophenone in 300 ml of diethyl ether are added dropwise to this solution at boiling heat over a period of 4 hours (vigorous, mechanical stirrer necessary; a viscous paste is formed). The mixture is then heated to reflux for a further hour, then cooled to about 5° C. and a solution of 50 ml of acetic acid and 100 ml of Et2O is next added dropwise under N2 at this temperature. About 500 ml of H2O are subsequently added dropwise and the organic phase is separated off. The aqueous phase is extracted once again using Et2O (2×400 ml), and the combined ethereal phases are washed with NaHCO3 solution, dried over MgSO4 and concentrated. The residue is distilled over a short Vigreux column.

Provenance & Evidence