Hydride of Benzoyle. 525 



tion completely, owing to the difficulty of separating and purify- 

 ing the products of the reaction. 



According to Gerhardt, hydride of cumyle, when heated with 

 potassium, disengages hydrogen, forming cumylide of potas- 

 sium : — 



2(G 10 H ll O, H) + K 2 =2(G lo H , i0,K)+H 2 . 



I have not succeeded in obtaining an identical result. If potas- 

 sium or sodium and cuminole be heated to the boiling-point of 

 the latter substance, a certain quantity of hydrogen is indeed 

 liberated, but far less than the volume demanded by the above 

 equation ; while this disengagement of gas is attended with a 

 more profound and irregular decomposition. This change also 

 occurs in the benzoyle series. When, however, cuminole and 

 sodium-amalgam are brought together, as before described, in 

 the presence of naphtha (cymole itself may be used), sodium- 

 cuminic alcohol and cumylide of sodium are formed in equivalent 

 proportions. Water acting upon these compounds on the one 

 hand regenerates the original hydride of cumyle, and on the 

 other liberates cuminic alcohol — 



}o + ^:h;o }+2 „ }8= 



£,0 H 13- 



Na_ 

 Sodium-cuminic Cumylide of 

 alcohol. sodium. 



Cuminic alcohol. Hydride of 

 cumyle. 



The cuminic alcohol thus derived is identical with that which 

 occurs in minute proportion in cumin oil, and which is also 

 formed artificially from cuminole by the action of alcoholic 

 potash. It boils at 244° C. Besides these two bodies, a some- 

 what viscid oil occurs in the product of the reaction. This oil 

 distils over at a high temperature, above 300° C, and is appa- 

 rently identical with Gerhardt's cumyle. It may be more readily 

 obtained in another way. When the product of the action of 

 sodium on cuminole is treated with chloride of cumyle, the 

 radical is formed, accompanied, however, with cuminate of 

 cymenyle. This mode of procedure, accomplished by Gerhardt, 

 gives therefore a mixed product; and this fact explains one or 

 two anomalies noticed by that chemist, especially in the action of 

 chloride of benzoyle upon his so-called "cumylure de potassium." 

 When the above-named bodies are mixed and heated, the change 

 proceeds to some extent as follows : — 



Phil. Mag. S. 4. No. 171. Suppl. Vol. 25. 2 N 



