Sixty-nine grams (3 gram atoms) of sodium is powdered under xylene in a 3-l. three-necked flask. The mixture is cooled, the xylene is decanted, and the sodium is washed twice with small portions of dry ether. One liter of absolute ether is then added to the powdered sodium. The flask is fitted with a mercury-sealed stirrer, an efficient reflux condenser, and a dropping funnel, the condenser and the funnel being protected from moisture with calcium chloride tubes. One hundred and thirty-eight grams (175 cc., 3 moles) of absolute ethyl alcohol is added drop by drop through the funnel (Note 1). After the alcohol has been added and there is no unchanged sodium (as evidenced by cessation of boiling) the flask is immersed in an ice-water bath, and a mixture of 306 g. (3 moles) of ethyl propionate and 438 g. (3 moles) of ethyl oxalate (Org. Syn. Coll. Vol. I, 1941, 261) is added slowly through the dropping funnel (Note 2).

After the ester mixture has been added, the stirrer is removed and the condenser set for downward distillation. The ether and the alcohol formed in the reaction are removed by heating on a water bath (Note 3). The residue, which usually solidifies upon cooling, is treated with 600 cc. of cold, 33 per cent acetic acid solution. The mixture is allowed to stand for several hours with occasional shaking in order to decompose the sodium derivative completely, and the product is extracted with four 500-cc. portions of ether. The ether solution is washed with 1 l. of water, with two 500-cc. portions of 10 per cent sodium bicarbonate solution, and finally with 1 l. of water. The ether is then removed by distillation, using a steam bath. The residue is fractionated through an efficient column (Note 4). The portion boiling at 114–116°/10 mm. is collected. The yield is 363–425 g. (60–70 per cent of the theoretical amount).