Acetone → CID 4301653

Participants

Reaction Steps

In a 2-liter three-neck round-bottom flask equipped with a dropping funnel and a paddle stirrer a solution of sodium ethoxide is prepared by reacting metallic sodium (7.74 g, 340.00 mmol, 1.2 eq) in anhydrous ethanol (800 ml) at ambient temperature until the metallic sodium has been completely consumed. A solution of diethyl oxalate (37.20 mL, 280.00 mmol, 1.0 eq) in acetone (10.30 mL, 280.00 mmol, 1.0 eq) is subsequently added dropwise at ambient temperature. The reaction medium is maintained with vigorous stirring for 2 hours. The reaction medium is subsequently concentrated under vacuum. The crude reaction product is diluted in water (200 ml). Ice (100 g) is added, followed by concentrated sulfuric acid (20 ml) in small portions, until a clear orange solution is obtained. The resulting aqueous phase is extracted with ethyl acetate (3×300 mL). The organic phases are combined, dried over MgSO4 and then concentrated under vacuum. The crude reaction product is dried under vacuum to give, quantitatively, the expected product (m=44.71 g).

Provenance & Evidence