526 Mr. A. H. Church on some Reactions of 



G 10 H 13 \ n , G 10 H»O"\ lO € 7 H 5 0~l 

 Na/ e+ NaJ" +3 t C1J- 



minic Cumylide of 

 sodium. 



\ e e>°H»e-i 2 Na"> 



Sodium-cummic Cumylide of 

 alcohol. sodium. 



€ 10 H 13 1 r, . C 10 H ll 9l , Na' 

 G 7 H 6 9 



Benzoate of Cumylide of 



eumenyle. benzoyle. 



Two methods of obtaining benzoic alcohol, in addition to the 

 process given above, have been described. M. Cannizzaro origi- 

 nally prepared this body by the action of alcoholic potash upon 

 oil of bitter almonds; but M. Friedel* has lately procured it 

 from the same substance by the simultaneous action of water 

 and sodium (sodium-amalgam). These somewhat analogous 

 reactions may be thus formulated : — 



2€ 7 H 6 + KHO=G 7 H 8 0-fC 7 H 5 K0 2 . 



€ 7 H 6 "9 + Na 2 + 2H 2 9=€ 7 H 8 + 2NaHO. 



Sometimes, however, chiefly when a modification of Friedel s 

 process is employed, along with benzoic alcohol, a white crystal- 

 line substance is formed, which I have made the subject of further 

 investigation. 



Conjoint Action of Sodium and Water on Hydride of Benzoyle. 



Into an intimate mixture of 10 parts of pure hydride of ben- 

 zoyle and 1 part of water, such an amount of sodium-amalgam 

 is to be added as shall contain 5 parts of sodium, the materials 

 being repeatedly shaken with gradual addition of 2 more parts 

 of water. The flask in which the experiment is made, after the 

 addition of some more sodium-amalgam, should be connected 

 with an apparatus from which hydrogen is being disengaged, and 

 then set aside for ten days or a fortnight, during which time it 

 should be frequently agitated, on each occasion a few drops of 

 water being poured in. The reaction being over, the flask will 

 be found to contain an aqueous solution of soda, benzoate of 

 sodium, together with a semisolid cake chiefly consisting of 

 benzoic alcohol and a new white crystalline substance, which 

 may either be gradually eliminated from the mass by repeated 

 treatments with very dilute boiling alcohol, or be freed from the 

 bodies accompanying it by repeated digestions with strong soda 

 solution. The substance thus purified having been once recry- 

 stallized from dilute boiling alcohol, is to be washed with water, 

 dried at 100° C, washed once with cold absolute ether, and 

 then twice recrystallized from the same liquid heated to ebulli- 

 tion. 



* Comptes Rendu.?, vol. Iv. p. 54. 



