Ethyl n-hexylmalonate

Ethyl malonate (160 g., 1.0 mole) is added with stirring to a solution of 23 g. (1.0 gram atom) of sodium in 400 ml. of absolute ethanol (p. 142). The mature is warmed on a steam bath, and 165 g. (1.0 mole) of n-hexyl bromide is added gradually. The mixture is heated for 4 hours on the steam bath, after which it is neutral and most of the ethanol is then distilled off with stirring to prevent bumping. The residue is dissolved in water the oily layer is separated, washed with water, and dried over calcium chloride. Fractional distillation of the oil yields 170 g. of ethyl n-hexylmalonate, b.p. 140-147°/15 mm. Redistillation gives a 73% yield boiling at 268-270°/749 mm. 

---