128 



Dr. T. E. Thorpe on the 



[Dec. 16, 



and its formation from the bromide by the action of ammonium alcoholate 

 may be thus represented : — 



C 6 H J {C 2 H 1 Br+^^Jo=C 6 H 3 {C 2 H 4 -0-C 2 H 3 + XH J Br. 



For this substance I propose the name styrolylethyl ether. It is a co- 

 lourless, mobile, fragrant-smelling liquid, boiling constantly at 187°, of 

 specific gravity 0*9310 at 21°*9, slightly soluble in water, and burning 

 with a strongly luminous flame. 



When heated for a few hours with a concentrated solution of hydriodic 

 acid in a sealed tube to about 120°, it was completely decomposed, and on 

 distilling the liquid from a water-bath, a quantity of ethyl iodide, boiling at 

 73°-75°, and easily recognizable by its characteristic alliaceous odour, 

 distilled over ; the presence of the alcohol rest in the new ether was thus 

 demonstrated. The remainder of the liquid, containing the greater portion 

 of the hydriodic acid and possibly the alcohol or its corresponding iodide, 

 was treated with dilute caustic soda, when a heavy oily liquid separated out. 

 This liquid was repeatedly washed with water and dried over calcium 

 chloride. On distilling it, the greater portion of the liquid boiled between 

 300° and 310°, but with evident decomposition, iodine being evolved. The 

 compound in all probability was the iodide corresponding to the bromide 

 originally taken, already described by Berthelot. 



C 6 H s {C 2 H 4 -0-C 2 H 5 + 2Hl"=C 6 H 5 {C 2 H J I+C 2 H 5 I+H 2 0. 



The very small quantity of substance at my disposal prevented me from 

 more accurately investigating the nature of this reaction, or the properties 

 of the iodine compound formed. 



I next sought to obtain the alcohol, C 6 H.{C 2 H 5 0, already described 

 by Berthelot as a colourless liquid of an agreeable aromatic odour, heavier 

 than water, and boiling at about 225°. I attempted to prepare the acetate, 

 intending to decompose the compound with caustic potash. Fifty grms. 

 of the bromide diluted with double its volume of absolute alcohol were 

 heated with about 40 grms. potassium acetate to 100° in a flask placed in 

 a water-bath. The liquid was then filtered from the mass of potassium 

 bromide, and again sealed up in tubes with a further addition of acetate, 

 and heated to 120°-130° for an hour or two. On cooling, the tubes were 

 reopened and the contents treated with water, and the non-miscible portion 

 separated and dried over calcium chloride. On standing over the calcium 

 chloride, a crystalline precipitate was slowly formed, which was afterwards 

 proved to be the compound of ethyl acetate and calcium chloride. On 

 submitting the dehydrated liquid to distillation, a further quantify of ethyl 

 acetate came over at 72°-74°. The next fraction, boiling between 

 140° and 150°, was found to consist chiefly of styrol ; the quantity, however, 

 was so small that in all probability it was not a product of the reaction, 

 but existed already formed in the bromide used for the experiment. The 

 next and main fraction of the distillate came over between 180° and 1 90°, and 

 on repeated rectification a constant boiling-point of 185°-186 c was obtained. 



