512 MM. Wurtz and Kekule on Phenole. 



of phosphorus, it is converted into bichloride, € 6 H 10 C1 2 . This 

 is a dense oil, which by the action of caustic potash is converted 

 into a chloride, € 6 H 9 CI. 



When oxide of mesityle is treated with sodium-amalgam it is 



reduced, and there is formed some mesitic ether, r±6 u\i r^« This 



is a colourless liquid boiling at 206°, and with a strong odour of 

 camphor. It is decomposed partially by distillation, giving some 

 products of condensation. 



What has hitherto been known as phorone has been an impure 

 product. It is best prepared by rectifying that part of the ori- 

 ginal product which passes between 180° and 205°. It crystal- 

 lizes in long friable prisms of greenish-yellow colour, and with 

 an odour like geranium. Treated with perchloride of phosphorus 

 this body yields chloride of phoryle, € 9 H 13 CI, which, treated in 

 turn with potash, regenerates phorone. 



Simultaneously, but quite independently of each other, Wurtz 

 and Kekule have described a reaction by which the aromatic hy- 

 drocarbons may be converted into their corresponding phenoles*. 

 When sulphobenzolic acid, or one of its salts, is fused with caustic 

 potash, it splits into sulphurous acid (which combines with the 

 alkali) and the corresponding phenole. The decomposition is best 

 effected at a temperature of from 250° to not exceeding 300° C. ; 

 and the residual mass on being treated with hydrochloric acid 

 liberates quantities of sulphurous acid, while phenole floats on 

 the acid solution. It is readily obtained pure, and its quantity 

 is almost the theoretical amount. The decomposition may be 

 thus written : 



€ 6 H 5 SO 3 K + KHO= SO 3 K 2 + C 6 H 5 , HO. 



Sulphobenzolate Sulphite of Phenole. 



of potassium. potassium. 



Wurtz has also found that sulphonaphthalic acid undergoes a 

 similar change, yielding sulphite of potassium, and probably 

 naphthylic alcohol. 



Kekule has observed that the sulpho-acids of phenole by 

 similar treatment undergo the same reaction and furnish deriva- 

 tives of benzole in which two atoms of hydrogen are replaced by two 

 of hydroxyle. One of the two isomeric modifications of sulpho- 

 phenylic acid passes into pyrocatechine, and the other into 

 resorcine — 



G6H4 {f©3H' G6H4 {9H 



* Comptes Rendus, vol, lxiv. pp. 748 & 752. 



