338 MESSRS. E. l^ANKLAND AND B. F. DUPPA'S 



VI. Action of Zinc upon a Mixture of Ethylic Iodide and Amylic Oxalate. 



Equivalent proportions of amylic oxalate and ethylic iodide were digested at 50° to 

 60° with excess of granulated zinc for several days. The reaction proceeded with 

 extreme sluggishness, and was not completed before the expiration of a week. The mass 

 being then mixed with water and submitted to distillation, an oily liquid passed over, 

 which on rectification was ultimately resolved into amylic alcohol and an ethereal liquid. 

 Submitted to analysis the latter yielded the following results :-— 



I. -2508 grm. gave '5999 grm. carbonic anhydride and "2475 grm. water, 

 II, '3299 grm. gave '7850 grm. carbonic anhydride and -3237 grm. water. 



These numbers agree closely with those calculated from the formula of amylic dieth- 

 oxalate, ^ t. ^ (CEtgHo 



C11H22O3, or 1^ J 



Ayo 



Calculated. Found. 



A ^ ^ A ^. 



I. II. Mean. 



di . . 132 65-34 65-23 64-90 65-07 

 H22 • . 22 10-89 10-96 10-90 10-93 

 O3 . . 48 23-77 24-00 



202 100-00 100-00 



The two consecutive reactions by which amylic diethoxalate is produced are expressed 

 in the following equations : — 



|C O Ayo_^2n,+4Et 1= j^ ^*^(^ ^^"^*)+Zn"Et Ayo+2Zn I^ ; 

 IC O Ayo (C O Ayo 



Amylic Amylic zincmonethyl- Zincethylo- 



oxalate. diethoxalate. amylate. 



(C Et,(0 Zn"Et) o ^|C Et,. Ho ^^ jj ^^„ jj 



(CO Ayo ' ICOAyo^ ^ ^ 



Amylic zincmonethyl- Amylic dieth- Zincic 



diethoxalate. oxalate. hydrate. 



Amylic diethoxalate is a colourless, transparent, and slightly oily liquid, possessing a 

 fragrant odour of a somewhat amylic character. It is insoluble in water, but miscible in 

 all proportions with alcohol and ether. Its specific gravity is -93227 at 13° C. It boils 

 constantly at 225° C. A determination of its vapour-density gave the following data : — 



Weight of amylic diethoxalate -1999 grm. 



Observed volume of vapour 49-8 cub. centims. 



Temperature of bath 246° C. 



Height of barometer 752 millims. 



Difference of height of mercury inside and outside tube . . .104 millims. 



Height of spermaceti column reduced to millimetres of mercury 14-24 millims. 



These numbers indicate a density of 6-74, the above formula requiring 6-97. 



