Ethyl (1-phenylethylidene)cyanoacetate, which is also known as , α-cyano-β-methyl-, ethyl ester, could be produced through the following synthetic routes.

In a 5-l. round-bottomed flask, 500 g. (5.3 moles) of chloroacetic acid is dissolved in 700 cc. of water. The solution is warmed to 50° and neutralized with anhydrous sodium carbonate of which about 290 g. (2.7 moles) is required (a slight excess of sodium carbonate is not disadvantageous). Meanwhile 294 g. (5.8 moles) of sodium cyanide (97 per cent) is dissolved in 750 cc. of water warmed to 55°. The sodium cyanide solution is then added to the sodium chloroacetate solution, which has been cooled to room temperature, with rapid mixing of the two solutions and cooling under the water tap. The temperature rapidly rises; when it reaches 95° the solution should be cooled by adding 200 cc. of cold water and this repeated, if necessary, until the temperature no longer rises. The solution is heated to the boiling point and boiled for five minutes, and finally cooled with running water for one-half hour.

The solution is filtered if not clear, and the cyanoacetic acid is set free (Hood) by adding with thorough stirring 694 g. (600 cc., 5.8 moles) (a slight excess) of commercial hydrochloric acid (sp. gr. 1.156). The solution is evaporated on a water bath at 60–70° under a pressure of 20–30 mm. and the evaporation continued until practically no more distillate comes over. To the residue is added 600 cc. of 95 per cent alcohol. The solution is filtered from the sodium chloride, and the residue is washed with another 500-cc. portion of alcohol.

On evaporating the alcoholic solution under reduced pressure from a water bath held at 50–60°the residue weighs about 540 g. A mixture of 600 cc. of absolute alcohol (p. 249) and 10 cc. of concentrated sulfuric acid is then added. The mixture is then heated on the water bath under a reflux condenser for three hours. The excess of alcohol and some of the water formed are removed by distillation under reduced pressure and the residue again heated for two hours with 300 cc. of absolute alcohol and an additional 4 cc. of concentrated sulfuric acid. The alcohol is removed by distillation under reduced pressure, and when the ester has cooled to room temperature, the sulfuric acid is neutralized with a concentrated solution of sodium carbonate; the ester (upper layer) is separated, and the aqueous solution extracted with ether, or preferably benzene; about one-tenth of the yield is in the extract. The combined products are placed in a 1-l. distilling flask and distilled under reduced pressure after the solvent and alcohol and water have been removed. The ester is collected at 94–99°, chiefly at 97–98°/16 mm. The yield of a product analyzing about 97–98 per cent ethyl cyanoacetate amounts to 474–492 g. (77–80 per cent of the theoretical amount).