(A) Ethoxyacetic Acid.—In a 2-l. round-bottomed flask, provided with a reflux condenser 70 to 80 cm. long, is placed 1250 cc. of absolute ethyl alcohol (Note 1). Through the condenser tube 69 g. (3 gram atoms) of metallic sodium is added rapidly enough to keep the alcohol refluxing gently. When the sodium has completely dissolved, a solution of 142 g. (1.5 moles) of chloroacetic acid in 180 cc. of absolute alcohol is added slowly in 20-cc. portions to the sodium ethoxide solution (Note 2). After all the acid has been added, the mixture is heated gently for ten minutes. The excess alcohol is removed as completely as possible by distilling from a steam bath and finally by passing steam into the residue. The aqueous solution is cooled, and 140 cc. (1.7 moles) of concentrated hydrochloric acid (sp. gr. 1.19) is added. The sodium chloride is removed by filtration with suction and is washed with two 50-cc. portions of ether. The original filtrate is saturated with dry sodium sulfate (30–35 g.) and is then extracted with the ether which was used for washing the precipitate, together with an additional 100 cc. of ether. The ether is separated from the aqueous layer, and the latter is extracted four times with 100-cc. portions of fresh ether. The ether is removed by distillation from a steam bath, and the residue is distilled under reduced pressure, using a 500-cc. Claisen flask equipped with a 500-cc. receiver. The acid boils at 109–111°/17–18 mm. and weighs 115–116 g. (74 per cent of the theoretical amount). By redistilling the low-boiling fraction and collecting the portion boiling at 150–210°, there is obtained an additional 7–10 g. of material which is chiefly ethoxyacetic acid and may be combined with the main fraction for conversion to the ester.

(B) Ethyl Ethoxyacetate.—The ethoxyacetic acid, which should amount to about 125 g. (1.2 moles), is placed in a 750-cc. Erlenmeyer flask containing 230 cc. (3.9 moles) of absolute ethyl alcohol. The flask is set in a pan filled with cold water (Note 3), and dry hydrogen chloride is passed into the mixture. After the mixture becomes saturated (Note 4) it is allowed to stand twenty-four hours to ensure the completion of the reaction at room temperature (Note 5). The solution is cooled, and a saturated solution of sodium carbonate is added cautiously and with stirring to avoid excessive foaming. The addition is continued until the mixture is faintly alkaline to litmus; an excess of sodium carbonate lowers the yield and should be avoided. The ester is extracted with four 100-cc. portions of ether; the extract is dried with 25 g. of anhydrous potassium carbonate, and the ether is distilled from a steam bath. The residue is distilled at ordinary pressure. The yield of ester boiling at 153–155° is 110–115 g. (55–58 per cent of the theoretical amount based on the chloroacetic acid, or 69–72 per cent based on the ethoxyacetic acid).