192 Messrs. Frankland and Duppa On the Acids [April 27* 



off at a gentle heat. On the subsequent application of a higher tempera- 

 ture, water, accompanied by amylic alcohol, amyl iodide, and an ethereal 

 liquid, distils over, the three latter forming a mixture, the separation of 

 which into its component parts presents rather formidable difficulties. 

 After drying with chloride of calcium, this oily mixture begins to boil at 

 about 132 C.; the product first passing over consists principally of amylic 

 alcohol, mixed with amyl iodide. Afterwards the thermometer rapidly 

 rises to 200 C., between which temperature and 205 C. a considerable 

 section of the remaining liquid, which we will call A, passes over. There 

 then occurs a further rapid rise of temperature until the thermometer 

 remains stationary between 222 and 226. The section collected between 

 these points we will call B. Finally, the temperature rises to 260-264, 

 between which points the remaining liquid (C) passes over. By repeated 

 fractional distillation, the larger portion of the section A was obtained at 

 the nearly fixed boiling-point of 203 C. This liquid was submitted to 

 analysis, and yielded numbers closely corresponding with the formula 



C 9 H I8 0, 



Interpreted by further results detailed below, this formula resolves itself into 



C,H,, 



OH 

 O 

 OC 2 H 5 . 



The ethereal body with the lowest boiling-point produced in this reaction 

 is therefore ethylic amylohydroxalate, or oxalic ether in which one atom 

 of oxygen is replaced by one atom of amyl and one of hydrogen. This 

 body also stands in very close relation to lactic ether ; for if the atom of 

 methyl in lactic ether be replaced by amyl, ethylic amylohydroxalate is 

 produced. 



f CH 3 



I * 



c 2 ; OH c 2 



L ~o~~ I o 



> OC 2 H 5 I OC 2 II 5 . 



Lactic ether. Ethylic amylohydroxalate. 



The two stages in the production of ethylic amylohydroxalate are ex- 

 plained by the following equations : 



C 



i - -, i c r\ TT n TT "i r* TT "i 



OZn C.X, +3H 2 0=C 2 J OH +2 Zn [ g g+^jf } + s jf " ] O. 



OC 2 H - ^ 00 2 H 5 



Ethylic amylo- Zinc Amyl Amylic alcohol. 

 hydroxalak 1 . hydrate, hydride. 



