340 MESSES. E. FRANKLAJJD AND B. F. DUPPA'S 



Amylic diamyloxalate is doubtless produced by the following consecutive reactions : — 



rCOAyo z _^4A I ^ rCAy,(OZn"Ay) Zn"Ay Ayo+2Zn"I, 

 ICOAyo * ' ICOAyo ^ ^ / t 2 



Amylic Amylic zincmonamyl- Zincic amylo- 



oxalate. diamyloxalate. amylate. 



|CAy(0Z„"Ay)^2H,0={C^y|H»+AyH+Zn"H„, 

 ICOAyo ICOAyo 



Amylic zincmonamyl- Amylic di- Amylic 



diamyloxalate. amyloxalate. hydride. 



The second ether mentioned above boiled between 215° and 220° C; it was decom- 

 posed by alcoholic potash ; the potash-salt so obtained, heated with dilute sulphuric 

 acid, yielded to ether an oily acid possessing the characteristic odour of caproic acid. 

 This acid, boiled with argentic carbonate suspended in water, gave on filtration magnificent 

 nacreous plates of a silver-salt which were very sparingly soluble in water, only slightly 

 acted upon by light, in fact possessing all the properties of normal silver caproate, 

 and differing markedly from the isomeric silver diethacetate recently described by us*. 

 Submitted to analysis this salt yielded the following results : — 



•1517 grm. gave 'ITTG grm. carbonic anhydride, -0685 grm. water, and '0729 grm. 

 metallic silver. 



These numbers agree closely with those calculated from the formula of silver caproate, 

 as seen from the following comparison : — 



CfiHuAgO,, or |CBuH2 ^^ CAyOAgo 

 6 u B 2> (CO Ago, ' ^ 



Calculated. Found. 



Cg . . 72 32-29 32-02 



Hii . . 11 4-93 5-02 



Ag . . 108 48-43 48-06 



O2 . . 32 14-35 14-90 



223 100-00 100-00 



Unfortunately we did not submit to analysis the ether from which this caproic acid 

 was obtained ; but there can scarcely be a doubt that it was amylic caproate. We have 

 stated that it boiled between 215° and 220°. The boiling-point of amylic caproate is not 

 known; but ethylic caproate boHs, according to Fehling, at 162° C. ; consequently the 

 boiling-point of amylic caproate ought to be, according to Kopp's law, 216° C, a number 

 which lies between the points observed in the ether under consideration. 



It is thus evident that the three variations in the action of zincamylide upon an 

 oxalic ether, described above as giving rise to amylhydroxalic acid, ethyl-amylhydroxalic 

 acid, and diamyloxalic acid, do not exhaust the fertility of this reaction ; and the pro- 



* Philosophical Transactions, vol. clvi. p. 37. 



