332 MESSES. E. FEANKLAND AND B. F. DUPPA'S 



202 100-00 



The above formula might be interpreted as that of ethylic amylethoxalate, the rational 



formula of which would be 



(CAyEtHo 



tc O Eto ' 

 We were at first inclined to regard this as the actual constitution of the new ether, 

 believing it to be possible that ethylic oxalate and amylic iodide mutually decomposed 

 each other, producing a mixture of amylic and ethylic oxalates with the amylic and 

 ethylic iodides ; an analogous decomposition of mixed ethereal salts of oxygen acids has 

 been recently noticed ; but the test of experiment obliged us to abandon this view of the 

 reaction. We found, it is true, a remarkable depression of temperature, amounting to 

 9°-3 C. on mixing one atom of ethylic oxalate with one of amylic iodide ; but on submitting 

 the mixture to distillation, the thermometer rose to the boiling-point of amylic iodide 

 (147°) before ebullition commenced, thus showing that none of the much more volatile 

 ethylic iodide had been formed. No transfer of radicals therefore takes place when ethylic 

 oxalate is heated with amylic iodide ; and consequently no zincethyl can be formed when 

 this mixture is acted on by zinc. We therefore prefer to view the ether now under eon- 

 sideration as ethylic ethyl-amylhydroxalate, analogous in constitution to Wurtz's ethylic 



ethyl-lactate*. 



jCMeHEto (CAyHEto 



(COEto ' ICOEto • 



Ethylic ethyl-lactate. Ethylic ethyl-amylhydroxalate. 



On this view the following equations represent the formation of this ether : — 



rCOEto , ^ ,, , , , ^ fCAy(Zn"Ay)Eto , „ „ . . , o-z "t 

 lC0Et0+^^^ + ^^y^ = IcOEto +Zn"AyAyo+2Zn"I,: 



Ethylic Amylic l^incic amylo- 



oxalate. iodide. amylate. 



rCAy(Zn"Ay)Eto 2JJ o^fCAyHEto ^ jj 2n"Ho,. 

 ICOEto ^ ICOEto, ^ 



Ethylic ethyl- Amylic Zincic 



amylhydroxalate. hydride. hydrate. 



* It deserves to be mentioned that the identity of boiling-point between this ether and its isomer amylic 

 diethoxalate described below does not favour this view, since a comparison of the boiling-points of ethylic ethyl- 

 lactate with that of ethylic ethomethoxalate and methylic diethoxalate, its isomers, shows that the substitution 

 of ethyl for the hydrogen of hydroxyl is attended with a depression of the boiling-point equal to 8°-5 C, the 

 percentage composition of the compound remaining constant. 



