Phelps and Tillotson, Jr. — Cyanacetic Acid. 275 



Art. XXX. — On the Preparation of Cyanacetic Acid and 

 its Ester from Monochlor acetic Acid ; by I. K. Phelps 

 and E. W. Tillotsoist, Jr. 



[Contributions from the Kent Chemical Laboratory of Yale Univ. — clxxxiii.] 



Kolbe,* in synthetizing malonic acid, states that if the solu- 

 tion obtained by acting on chloracetic acid with potassium 

 cyanide be acidified with sulphuric acid and extracted with 

 ether, cyanacetic acid is obtained, which on boiling with potas- 

 sium hydroxide is converted to potassium malonate. Mullerf 

 obtained cyanacetic ester " boiling above 200° " by treating 

 chloracetic ester in alcoholic solution with potassium cyanide. 

 FinkelsteinJ used chloracetic ester and an aqueous solution of 

 potassium cyanide, boiling till all the ester had gone into solu- 

 tion, evaporating to dryness, acidifying the residue with hydro- 

 chloric acid and extracting with ether. On evaporation of the 

 ether cyanacetic acid was obtained. Meeves§ also acted on 

 chloracetic ester with potassium cyanide in a water solution, 

 evaporated, acidified with sulphuric acid, and extracted with 

 ether. The acid obtained on evaporation of the ether was 

 purified by treating with lead carbonate, filtering off the excess 

 of carbonate and insoluble lead malonate and decomposing the 

 solution of lead cyanacetate with hydrogen sulphide ; but as in 

 the case of the other investigators mentioned above, no results 

 were given by him showing the amount of cyanacetic acid 

 obtainable from a given weight of chloracetic acid. Grim- 

 aux and Tcherneak|| caused sodium chloracetate and potassium 

 cyanide to react, extracted the cyanacetic acid with ether 

 according to Meeves' procedure and obtained about 75 per 

 cent of the theoretical amount of cyanacetic acid. Yan't 

 HoffT states that he obtained a nearly theoretical yield from 

 chloracetic acid, but gave no definite information as to how it 

 was obtained. Fiquet** followed in general the same procedure 

 as Grimaux and Tcherneak, acidifying with hydrochloric acid 

 instead of sulphuric acid, and obtained 70 per cent of that theo- 

 retically possible. Noyes,ft after boiling chloracetic ester and 

 potassium cyanide with methyl alcohol, obtained 50 per cent 

 of the theoretical yield of cyanacetic ester, boiling within 

 limits of ten degrees. 



In a former paper^J it has been shown from the amount of 

 malonic ester obtained that sodium chloracetate and potassium 



*Ann., cxxxi, 348. f Ann., cxxxi, 350. 



JAnn., cxxxiii, 338. §Ann., cxliii, 201. 



|| Bull. Soc. Chim., xxxi, 338. ^ Berichte, vii, 1382. 



** Jour. Am. Chem. Soc, xxvi, 1545. ff Ann. Chim. [6], xxix, 439. 



XX This Journal, xxvi, 267. 



