Diethyl Malonate → Diethyl-2-[4'-(2",4"-dichloro-phenoxy)-phenoxy]-propionyl-malonate

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Reaction Steps

A 50% etheral solution of 35 g of 2-[4'-(2",4"-dichloro-phenoxy)-phenoxy]-propionyl-chloride is added under stirring dropwise to a mixture of diethyl-ethoxy-magnesium-malonate prepared from 17.6 g of diethyl malonate and 50 ml of ether. The addition of the acid chloride having been completed the reaction mixture is heated to boiling for an hour, cooled to room temperature and washed successively with 100 ml of 5% sulfuric acid, 100 ml of a 6% sodium bicarbonate solution and 100 ml of water. The etheral phase is evaporated, the excess of the malonic acid ester is distilled off, the residue is admixed with 100 ml of benzene, subjected to chromatography on a silica column and eluted with 50 ml of benzene. The united eluates are evaporated. Thus 35 g of the desired compound are obtained in the form of a slowly solidifying product. Mp.: 46°-50° C. Yield 75%.

Provenance & Evidence