Hydrochloric Acid → HCID 19871659, compound

Participants

Reaction Steps

127.2 g (1.2 mol) of sodium carbonate and 4.6 g (0.02 mol) of benzyltriethylammonium chloride are suspended in 800 ml of acetonitrile. While stirring there is added dropwise thereto within 8 hours a solution of 150.5 g (1 mol) of methyl 4-chloroacetoacetate and 138.8 g (1.5 mol) of chloroacetone in 200 ml of acetonitrile. The mixture is stirred at 20°-25° C. for a further 15 hours. The reaction mixture is poured into 750 ml of 2N HCl (pH value=1) and extracted three times with 300 ml of ether. The combined organic phases are dried over magnesium sulphate and concentrated on a rotary evaporator. The residue is treated with 200 ml of ether, the precipitated 2,5-bimethoxycarbonyl-1,4-cyclohexanedione is filtered off under suction and the filtrate is again concentrated. The crude product is column chromatographed on silica gel with ether/hexane 1:1 and gives 32.28 g (15.6%) of methyl 4-chloro-2-acetonylacetoacetate.

Provenance & Evidence