SYNTHETICAL RESEAECHES ON ACIDS OF THE LACTIC SERIES. 327 



to ascertain whether the same replacement could be effected by an atom of each of two 

 different monad alcohol-radicals. We endeavoured to accomplish this by acting with 

 zinc upon a mixture consisting of one atom of ethylic oxalate and one atom each of the 

 methylic and ethylic iodides, by which we hoped to obtain an acid of the following 

 composition, 



,H,oO.={^Et 



/-.XT r* iJEtMeHo 



Experiment completely proved the practicability of this reaction ; and its result even 

 exceeded our expectations, since not only was the ether corresponding to the above 

 acid formed with the greatest facility, but it was produced almost to the complete 

 exclusion of the ethers of diethoxalic and dimethoxalic acids. 



200 grammes of ethylic oxalate were mixed with the proper atomic proportions of 

 methylic iodide and ethylic iodide, and were digested with granulated zinc for several 

 days at a temperature of from 35° to 40° C, until the supernatant liquid became oily, and 

 solidified to a crystalline mass on cooling. Water being now added till effervescence 

 ceased, the whole was submitted to distillation in an oil-bath. With the exception of 

 a small quantity of the mixed ethylic and methylic iodides that had escaped decompo- 

 sition, the distillate consisted of a homogeneous liquid composed of water, ethylic and 

 methylic alcohols, and an ethereal body, which last was separated by repeated agitation 

 with large volumes of ether and subsequent rectification. In this manner there was 

 obtained a large quantity of a liquid which boiled constantly at 165°'5 C, and yielded 

 on analysis numbers very closely corresponding with the formula 



C,H,.03={CE' 



EtMeHo 

 Eto 



I. •2843 grm. gave '5990 grm. carbonic anhydride and '2498 grm. water. 

 II. '2936 grm. gave '6188 grm. carbonic anhydride and -2584 grm. water. 



The production of this ether is explained in the following equations : — 



|C O Eto 42n+2Et I.f2Me I = (^ ^' ^'(^ Z^"M^)+Zn"Et Eto+2Zn"I,; 

 ICOEto -r - IcOEto t 2. 



EthyUc Ethylic zincmonomethyl 



oxalate. ethomethoxalate. 



2t2 



