— 154 — V 



ethyl alcohol. The nitrite forms an unstable golden-yellow oil with a 

 peculiar odour, reminding somewhat of turpentine: b.p. 72,5 to 73° (19 mm.), 

 d^ 1,045, « D17 o + 6,80°. Holmberg has not yet discovered a suitable 

 method for preparing from the nitrite the corresponding alcohol. d-Phenyl- 

 ethyl alcohol had been produced in somewhat larger quantity. Its con- 

 stants are given as follow: b.p. 98,5 to 99° (20 mm.), d^ 1,018, « D15 o + 5,00°. 

 In the experiment for preparing Z-phenylethylalcohol from d-phenylethyl- 

 amine the cooling-process had not been carried out sufficiently thoroughly, 

 with the result that the alcohol generated only gave « D17 o — 4,40°. It is 

 therefore certain that when phenylethyl alcohol is formed, racemisation 

 takes place, in proportion as the reaction temperature is higher. Con- 

 version of the ^-phenylethyl alcohol into the bromide by saturating it with 

 hydrobromic acid gave rise to inactive a-bromethylbenzene. Z-Phenylethyl 

 alcohol and phosphorus pentabromide led to a bromide with a faint 

 dextrorotation: a D uo + l,50°. The action of silver oxide upon the alcoholic 

 solution of et-bromoethylbenzene resulted in the ethylether of phenylethyl 

 alcohol, a colourless oil with an agreeable odour (d^ 0,928). 



Cinnamic alcohol. As the crude material for an investigation into 

 the transposition of ethylene linkings, H. Beaufour 1 ) employed the methyl- 

 ether of cinnamic alcohol, the preparation of which he describes as fol- 

 lows: 40 grams sodium amide, reduced to fine powder under benzene or 

 ether, is gradually diluted in a flask with a solution of 150 grams cinnamic 

 alcohol in 200 cc. benzene. In the course of about half an hour the 

 alcoholate has been precipitated in the form of a solid mass. After this, 

 150 grams methyl iodide is gradually added, and part of the sodium iodide 

 which has separated out is drawn off. The cinnamyl methylether boils 

 at 227° (117° at 16 mm.): d o 1,0037. The ethylether obtained by the same 

 method possesses the following constants: b.p. 127 to 129° (17 mm.), 

 d o 0,9938. 



Aldehydes. 



H. D. Law 2 ) has reduced by the electrolytical method a series of 

 aliphatic and aromatic ketones and aldehydes. Generally speaking, the 

 electrolytical reduction proceeds on the same lines as that with sodium 

 amalgam, but it has the disadvantage thas it does not permit work to be 

 carried on at high temperatures. Methylheptenone was reduced very slowly 

 in alkaline solution, but much more rapidly in sulphuric acid with lead 

 cathodes. The reaction-products detected were methylheptenol, an isomeric 

 oxide C 8 H 16 0, b.p. 127 to 129°, which has already been obtained by Wallach 3 ) 



^ Bull. Soc. chim. IV. 11 (1912), 648. 



2 ) Journ. chem. Soc. 101 (1912), 1016. 



3 ) Liebigs Annalen 275 (1893), 171. 



