— 173 — 



properties are recorded below: phenol-a-naphthyl urethane, m. p. 136 to 

 137° (after previous softening at 133°), o-cresol-«-naphthyl urethane, 

 m. p. 145° (not very definite), m-cresol-«-naphthyl urethane, m. p. 135 to 

 136°, p-cresol-a-naphthyl urethane, m. p. 287 to 288°, (softens at 120°), 

 carvacrol «-naphthyl urethane, m. p. 287 to 288°, saligenin-a-naphthyl 

 urethane, m. p. 283° (with evolution of gas after previous blackening at 

 281°), cinnamic alcohol-«-naphthyl urethane, m. p. 119 to 120°, menthol- 

 «-naphthyl urethane, m. p. 128° (drips at 124°), l-borneol-«-naphthyl ure- 

 thane, m. p. 132°, isoborneol-a-naphthyl urethane, m. p. 129°, «-terpineol- 

 «-naphthyl urethane, m. p. 151 to 152°, c?/cZohexanol-«-naphthyl urethane, 

 m. p. 139 to 140° (drips at 135°). 



The authors observe with regard to the above that in determining the 

 m. p. the heating must not proceed too slowly, because in that case the 

 substance gradually decomposes. Decomposition, however, also sets in 

 when the substance is kept for a long period. 



The naphthyl urethanes of geraniol, dihydrocuminic alcohol, terpineol, 

 and linalool were prepared by us some years ago 1 ). 



Menthol. Tschugaeff 2 ) has recently prepared d-menthol, m. p. 42°, from 

 the fraction of an esterfied buchu leaf oil boiling between 190 and 225°, by 

 reducing with sodium and purifying the resulting alcohol by means of 

 the xanthogenic anhydride compound. Boiling the dixanthogenide in 

 an alcoholic solution with potassium cyanide gave rise to the thio 

 anhydride (m. p. 147,5 to 148°; [«] D + 46,42°). The dixanthogenide appears 

 in the form of yellow needles, m. p. 92 to 92,5° ([«] D + 226,3°). 



Borneol. In the year 1867 Lauth and Oppenheim 3 ) discovered that 

 pinene hydrochloride (bornyl chloride), when heated with aniline to 150°, 

 yielded terecamphene (1-camphene); but J. W. Bruhl 4 ), upon repeating their 

 process, observed that when aniline was heated to 200° with the molecular 

 quantity of bornyl chloride, a violet mass was formed from which the chloride 

 was recoverable by steam distillation. No camphene had been formed 

 during the process. 



Recently, F. Ullmann and A. Schmid 5 ) have thoroughly investigated 

 this reaction, with the results set forth below: When molecular quantities 

 of aniline are allowed to act upon bornyl chloride at 200°, a little camphene 

 is formed, together with other products, but a large part of the chloride 

 remains unattacked. Working at 150° the bulk of the bornyl chloride 

 likewise remains intact, and an oily body (bornyl aniline) is formed, which 



!) Report October 1906, 41. 



2 ) Journ. Russ. phys. chem. Soc. 42 (1910), 714. Quoted from Chem. Zentralbl. 1910, II. 1709. 



*) Bull. Soc. chim. II. 8 (1867), 6. 



*) Berl. Berichte 25 (1892), 146. 



■) Berl. Berichte 43 (1910), 3202. 



