— 141 — 



the accumulation of a possibly-present foreign body as a result of distilla- 

 tion was out of the question. We then attempted, by oxidising with 

 chromic acid and bichromate of potassium, and by using phthalic anhydride, 

 formic acid, glacial acetic and sulphuric acids and semicarbazide, to iso- 

 late or accumulate a substance of some sort which would enable us to 

 infer the presence of a foreign body in addition to linalool, but again 

 without success. Finally we made the experiment of preparing a pure 

 linalool by splitting up linalylphenylurethane, a substance which can be 

 prepared without difficulty in the pure state. We caused 50 grms. of our 

 linalool to react with 40 grms. phenyHsocyanate. The resulting phenyl- 

 urethane crystallised from light petroleum in stout prisms, about 1 cm. 

 long, melting at about 64°. The phenyHsocyanate was split up by boiling 

 it for several hours with alcoholic potash and the resulting alcohol driven 

 off with steam. In order to remove the aniline which had also been 

 formed in the process of decomposing the ester, the distillate was shaken 

 up with tartaric acid solution. The alcohol prepared by this method 

 boiled at 199 to 200° and gave: d 15 o 0,8666, « D — 17°41', n D20O 1,46238, 

 mol. refr. found 49,12, calc. as C 10 H 18 O/r 48,97. 



Treated with phenyh'socyanate, the alcohol reverted into the phenyl- 

 urethane, m. p. 64°; when oxidised with bichromate and sulphuric acid it 

 reverted into citral. 



Hence the specific gravity of linalool is lower than has hitherto been 

 assumed to be the case. (We have observed di 5 o 0,869 to 0,873 in the 

 commercial article) 1 ). It should also be stated here that Tiemann 2 ) has 

 found similar constants in a specially purified linalool: b. p. 86 to 87° 

 (14 mm.), d 2 oo 0,8622, n D20O 1,46108. 



On ^-c?/c/ohexanol-r/-glucoside see p. 139. 



Borneol. J. Aloy and V. • Brustier') have found that when borneol- 

 vapours are passed over copper oxide heated to from 250 to 300°, camphor 

 is formed. At 300° the reaction is quantitative. When the temperature 

 is further increased the yields diminish until finally, at between 420 and 

 430°, a mixture of terpene hydrocarbons results. But, reversely, camphor 

 cannot be reduced to borneol by Sabatier's and Senderens's reduction method. 

 The reduction, however, may be accomplished with camphor oxime, by 

 passing the oxime-vapours, mixed with hydrogen, over nickel heated to 

 about 180 to 200°. In the course of this conversion bornylamine, 

 dibornylamine and camphylamine are generated in addition to ammonia. 



*) Gildemeister and Hoffmann, Die atherischen Ole, 2 nd Ed., Vol. I. .p. 370. 



2 ) Berl. Berichte 31 (1898), 834. 



3 ) Bull. Soc. chim. IV. 9 (1911), 733. 



