524 Mr. A. II. Church on some Reactions of 



Na/^+Hj" - H r 0+ Naj y ' 



Sodium-benzoic Benzoic alcohol, 



alcohol. 



CWei H\ o _G-H 5 01 ,H\ 



Benzoylide of Hydride of 



sodium. benzoyle. 



The correctness of these equations is abundantly confirmed by 

 every observation hitherto made — such as the amount of sodium 

 absorbed, the non-evolution of hydrogen either in the action of 

 sodium on the aldehyde or in the action of water upon the 

 sodium-compound ; the actual experimental production, as above 

 mentioned, of (about) 1 equiv. of benzoic alcohol and 1 equiv. 

 of benzoic aldehyde to 2 equivs. of hydrate of sodium; but above 

 all, the nature of the two chief final products, benzoic alcohol 

 and benzoic aldehyde, which may most reasonably be supposed 

 to owe their origin to the action of water upon their respective 

 sodium-compounds. It should, however, be here stated that 

 when sodium is heated with hydride of benzoyle, the action is 

 occasionally arrested when but half complete : it is difficult to 

 account for the phenomenon, except on the supposition that 

 benzoyle is formed instead of benzoylide of sodium. 



Since the sodium-compounds do not admit of accurate analysis 

 or complete separation from one another, I have not only iden- 

 tified the benzoic alcohol and aldehyde which they yield when 

 treated with water, with the common forms of these substances, 

 but I have examined the action of hydrochloric acid and of chlo- 

 ride of benzoyle upon them. 



When hydrochloric acid gas is passed through benzole in 

 which the sodium-compounds are suspended, chloride of tolu- 

 euyle (benzyle) is produced. This liquid, identified by Canniz- 

 zaro* with chlortoluole, boils at 185° C. It distils over with 

 some quantity of regenerated oil of bitter almonds. When, in 

 this experiment, chloride of benzoyle is substituted for hydro- 

 chloric acid, the benzole when distilled off, after separation of the 

 chloride of sodium, leaves as a residue a partly crystalline mass 

 which theoretically should contain benzoyle along with the ben- 

 zoyle-compoundof benzoic alcohol — the benzoate of toluenyle, 



e 7 Hn a , g 7 ipo\ . 9 £ 7 H 5 tn 



Na/ Na/ +Z CI J " 



£ 7H? lo+ G7H5 °l +* Na l 



G 7 H 6 OJ ^ + G 7 H 5 GJ + ~ CI J' 



Hitherto, however, I have not been able to verify this supposi- 

 * Jahresbericht, 1855, p. 621. 



