Rosolic Acid and Rosanilhie. 129 



2. Whether, the agent being one containing carbon of the fatty- 

 series, it is possible to get rosolic acid from phenol absolutely 

 free from cressylic alcohol ? 



In carrying out my design, I was at once met by the difficulty 

 of obtaining pure phenol. Even the best crystallized and co- 

 lourless specimens of carbolic acid now to be met with in com- 

 merce contain more or less cressylic alcohol. I am therefore 

 greatly indebted to Mr. C. Lowe, who kindly supplied me with a 

 splendidly crystallized specimen of pure hydrated carbolic acid*, 

 which by simple distillation is resolved into water and into 

 perfectly pure phenylic alcohol, which immediately solidifies in 

 the receiver. Pure phenol has a faint vinous smell, fuses at 

 42° C, and boils constantly at 184° C. (correct). It shows no 

 tendency to deliquesce, nor to get coloured in the air. 



Another specimen of phenylic alcohol was obtained by the de- 

 structive distillation of salicylate of lime (prepared from gaul- 

 theria oil). It presented the same physical characters as coal- 

 tar (phenol). Its boiling-point was found to be 184° C. (correct), 

 and its fusing- point 41° C.f 



The mixture of phenylic and cressylic alcohols employed in 

 the following experiments was obtained by repeated fractional 

 distillations from the higher-boiling portions of commercial 

 cressol. It was a colourless, highly refracting liquid of faint 

 pleasant smell, and boiling between 194° C. and 199° C. 



Lastly, I prepared some cressylic alcohol by treating perfectly 

 pure hydrochlorate of toluidine with nitrous acid, and heating 

 the resulting and diluted solution of hydrochlorate of diazotoluol 

 to ebullition. Under evolution of nitrogen, cressylic alcohol 

 separated out as a heavy brown oil, largely contaminated with 

 nitrocressylic acids. Treatment with tin and hydrochloric acid 

 destroyed these nitro-compounds ; and repeated washings and, 

 lastly, distillation over a small piece of sodium rendered cressylic 

 alcohol perfectly colourless. 



These substances were submitted to the action of peroxide of 

 manganese (Smith) and oxide of mercury (Jourdin) in the pre- 

 sence of caustic soda, likewise to the action of chloride of mercury 

 (Jourdin), sulphate of mercury, arsenic acid (Fol), and iodine. 



In every instance equal quantities of pure phenol and of the 

 mixture of phenylic and cressylic alcohols were employed, and 

 heated with the same weights of the aforesaid reagents under 

 conditions precisely alike, and observing the indications given 

 by the authors of these processes. Some of these experiments 

 have been several times repeated with altered proportions. 



* F. C. Calvert, Chem. Soc. Journ. xviii. p. 66. 



t According to determinations made by C. Schorlemmer : phenol melts 

 at 34°-35° according to Laurent. 



Phil. Mag. S. 4. Vol. 32, No. 214. August 183G. K 



