828 MESSRS. E. mANKLAND AlO) B. F. DIJPPA'S 



Calculated. Fotmd. 



, A 



I. II. in. IV. V. VI. Mean. 



22-88 22-75 23-05 22-89 



3-45 3-35 3-40 3-40 



51-22 51-34 51-26 51-31 51-38 51-30 



22-41 



100-00 



Attempts to produce ethylic dimethoxalate by digesting the free acid with absolute 

 alcohol at a temperature of 160° C. proved abortive, traces only of the ether being appa- 

 rently formed. Judging, however, from our subsequent success in obtaining ethylic 

 dimethoxalate as described below, we believe that the methylic ether would probably 

 be obtained by repeatedly agitating with ether the aqueous distillate obtained from the 

 crude product of the original operation, methylic dimethoxalate being evidently like 

 ethylic dimethoxalate, miscible with water in all proportions. Assuming the formation 

 of this ether, its production from the mutual action of zinc, methylic oxalate, and 

 methylic iodide, followed by that of water, would be expressed in the following equa- 

 tions : — 



fCOMeo , ry n , ,^, r [CMe2(0Zn"Me) , ^ „,, ,, 



[c O Meo + ^<+^^^ ^= IC O Meo + ^^ ^^ Meo+2Zn" I, : 



Methylic Methylic zincmonomethyl Zinomethylo- 



oxalate. dimethoxalate. methylate. 



Methylic zincmonomethyl Methylic Zincic hydrate, 



dimethoxalate. dimethoxalate. 



Dimethoxalic acid exhibits the same composition as Staedeler's acetonic acid, Wdbtz's 

 butylactic acid, and the oxybutyric acid obtained by Feiedel and Machuca. The 

 relations of these acids to each other will be discussed at the conclusion of this paper. 



III. Action of Zinc upon a Mixture of Ethylic Iodide and Methylic Oxalate. 



This reaction was performed in exactly the same manner as the last. On the addition 

 of water, the product yielded, on subsequent distillation, a considerable quantity of an 

 ethereal body, which distilled over together with the ethylic iodide that had not been 

 acted upon. The addition of water to the distillate effected an approximate separation 

 of the ethereal from the alcoholic portion ; the former was then decanted and distilled 

 for the purpose of separating alcohol and ethylic iodide. When the temperature of 

 ebullition rose to 100° C, the liquid left in the retort was placed over calcic chloride for 

 twelve hours, after which it was again submitted to distillation, when its boiling-point 

 almost immediately rose to 165° C. (barom. 758-2 millims.), at which temperature the 



