458 Messrs. Frankland and Duppa. Synthetical [Nov. 16, 



November 16, 1865. 

 Lieut.-General SABINE, President, in the Chair. 



In accordance with the Statutes, notice of the ensuing Anniversary 

 Meeting for the election of Council and Officers was given from the Chair. 



Mr. Bowman, Dr. Frankland, Mr. F. Galton, Sir John Lubbock, and 

 Mr. Spottiswoode, having been nominated by the President, were elected 

 by ballot Auditors of the Treasurer's accounts on the part of the Society. 



Mr. George Robert Gray was admitted into the Society. 



The following communications were read : 



I. " Synthetical Researches upon Ethers. Synthesis of Ethers from 

 Acetic Ethers." By E. FRANKLAND, F.R.S., Professor of 

 Chemistry in the Royal Institution of Great Britain, and in the 

 Royal School of Mines, and B. F. DUPPA, Esq. Received July 

 13, 1865. 



(Abstract.) 



In a recent note * we have briefly described the synthesis of butyric and 

 diethacetic ethers by acting consecutively upon acetic ether with sodium 

 and the iodide of ethyl. In the present paper we have the honour to lay 

 before the Royal Society the detailed results of one section of this research, 

 embracing the action of sodium and the iodides of methyl, ethyl, and amyl 

 upon acetic ether. 



I. Action of Sodium and Ethyl Iodide upon Acetic Ether. 



When acetic ether is treated with sodium at a temperature gradually 

 rising to 120 C., hydrogen is evolved, and a thick brownish liquid pro- 

 duced ; the latter solidifies on cooling to a yellowish mass, presenting the 

 appearance of beeswax. On digesting this solid mass with ethylic iodide 

 at 100 C. for several hours, a number of products are formed, which on the 

 addition of water, may be distilled off from a residue consisting chiefly of 

 iodide of sodium. The distillate can readily be separated into an aqueous 

 and an oily portion. The latter then presented the appearance of a light 

 straw-coloured oil, possessing a pleasant and fragrant odour. It was washed 

 and then dried over chloride of calcium, and submitted to fractional distil- 

 lation, by which traces of alcohol, acetic ether, and ethyl iodide were 

 effectually removed from the other products, which now boiled between 

 120 and 265 C. We have described the constituents of this complex 

 liquid under two distinct heads, viz. : 



1st. Products depending upon the duplication of the atom of acetic 

 ether. 



2nd. Products derived from the replacement of hydrogen in the methyl 

 of acetic ether by the alcohol-radicals. 



In order successfully to separate the two products from each other, and 

 * Proceedings of the Royal Society, vol. xir. p. 198. 



