M. Linnemann on Benzhydrole. 531 



formation of naphthylmercaptan ammonium, takes place in con- 

 sequence of oxidation ; thus 

 C 20 H 7 1 



NH 4 r S2+0=C20H7S2+HO+NH3 - 



__ , ■ -^ Bisulphide 



]S apthylmer- of naphthyle. 



captan ammonium. 



Linnemann* has continued his investigations f of benzophe- 

 none, € 13 H 10 O, the acetone corresponding to benzoic acid. He 

 finds that benzoate of lime, when distilled with lime, yields this 

 body along with benzole in about the proportion of two of the 

 latter for one of the former. Benzophenone has a great ten- 

 dency to crystallization, and is readily obtained in large crystals. 

 It unites with bromine, but not without the formation of hydro- 

 bromic acid, and the bodies formed are not of a very definite 

 nature. 



Linnemann had previously found that by the action of nascent 

 hydrogen on benzophenone a body was formed which he called 

 Benzhydrole, and assigned to it the formula G 13 H 14 9, which sub- 

 sequent analyses show ought to be € 13 H 12 O. This body has 

 many of the properties of a monatomic alcohol, but differs in 

 that, when oxidized (as, for example, by chromic acid) it repro- 

 duces benzophenone, and not an aldehyde. If the benzhydrole 

 is treated by strong nitric acid, oxidation first takes place, form- 

 ing benzophenone, which is then converted into binitrobenzophe- 

 none, C 13 H 8 (N0 2 ) 2 0. 



Benzophenone thus behaves exactly like acetone. That sub- 

 stance, when treated by nascent hydrogen, yields an alcohol 

 isomeric but not identical with propylic alcohol, and called ac- 

 cordingly isopropylic alcohol. This isopropylic alcohol when 

 oxidized yields the body acetone from which it was formed, 

 instead of propylic aldehyde as is the case with ordinary pro- 

 pylic alcohol. Benzhydrole also differs in another important 

 respect from ordinary alcohol, inasmuch as it readily forms with 

 bromine bibrominated benzhydrole, C 13 H 10 Br 2 0. This body con- 

 sists of a light glistening white mass, which is seen, under the 

 microscope, to consist of small acicular crystals. 



Benzhydrole resembles the alcohols in that it readily forms 

 compound ethers ; it differs in that, as yet, it has not been pos- 

 sible to form a chloride or iodide of the alcohol. The action of 

 the chloride of phosphorus is simply a withdrawal of water with 



the formation of benzhydrolic ether, pi 3 tth rO. This body 



is also formed by keeping benzhydrole for sometime at the boil- 



* Liebig's Annalen, January 1864. 

 t Phil. Mag. S. 4. vol. xxv. p. 539. 



