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III. Synthetical Researches on Ethers. — No. 1. Synthesis of Mhers from Acetic Ether. 

 By E. Feankland, F.R.S., and B. F. Duppa, Esq. 



Eeceived July 13, — Read November 16, 1865. 



In his researches upon lactic acid Wurtz* contends with considerable force for the diba- 

 sicity of this acid, supporting his view by the transformation of monobasic into dibasic 

 lactic ether by the consecutive action of sodium and iodide of ethyl, as expressed in the 

 following equations : 



2 a 



fCH3 

 H 

 OH 



+Na2=2a 



o 



OCgH, 



Lactic ether. 



fCH3 



H • 



ONa 



O 

 IOC2H5 



y 



+H, 



C, 



CH3 

 H 



ONa 

 O 



+aHj=a 





Sodio-lactic ether. 



rcH3 



H 



OCgHs+Nal 

 O 

 IOC2H5 



Sodio-lactic ether. Dibasic lactic ether. 



During the prosecution of our researches upon acids of the lactic series f, we have 

 obtained several so-called dibasic ethers of this description ; but before finally deciding 

 upon the interpretation to be put upon such reactions, it appeared advisable to ascertain 

 the efiect of the same reagents upon a well-defined monobasic ether. For this purpose 

 acetic ether was selected, and was treated, first, with sodium, and then with the iodides 

 of ethyl, methyl, and amyl respectively. The results, although not strictly analogous 

 with those obtained under similar circumstances with ethers of the lactic series, are 

 highly remarkable. We have already briefly referred to them in a note presented to 

 the Royal Society in April 1865 J. 



Action of Sodium and Ethyl Iodide upon Acetic Ether. 



The acetic ether used for this and the succeeding reactions was made as follows :-^— 

 6000 grms. of previously dried and fused sodium acetate was broken into small pieces 



* Ann. de Ch. et de Phys. t. lix. p. 161. 



t Proceedings of the Eoyal Society, vol. xii. p. 396 ; vol. xiii. p, 140 ; vol. xiv. pp. 17, 79, 83, 191, and 197. 

 t I>nd. vol. xiv. p. 198. 

 MDCCCLXVI. G 



