M. Bodart on Phorone. 189 



The formation of phoroue takes place according to the equation 

 C24 H24 024=Ci8 Ri* 0^ + 6CO2 + 10HO. 

 Grape-sugar. Phorone. 

 By treating phorone with pentachloride of phosphorus, the chlo- 

 ride of phoryle,C^^ H^^Cljis formed; it is an oil lighter than water, 

 boiling at 175°. By distilling phorone with anhydrous phos- 

 phoric acid, there passes over a limpid, highly refracting oil, of 

 an agreeable odour, and boiling at 150° — 160°. This is pro- 

 bably cumole, C'^ H'^j or a substance isomeric with it. 



M. Bodart suggests that the formula of Fremy's metacetone 

 should be C'^HisO^ instead of C^H^O. Its formation from 

 grape-sugar would then be thus expressed : — 



C24 JJ24 024_C18 tP^ 03-)-6C02 + 9H0. 



Grape-sugar. Metacetoue. 

 In support of this view, M. Bodart found that by distilling 

 this metacetone with anhydrous phosphoric acid, phoroue is 

 produced, 



CIS H15 03 + po5=Ci8 HI'* 0^-i-PO^ HO. 



Metacetone. Phorone. 



Prom its reactions, phorone must be considered as an alcohol 

 to which cumole stands in the same ]'elation as olefiant gas does 

 to common alcohol. The transformation of phorone into cumole 

 connects sugar with the cuminic acid series, and consequently 

 with the benzoic acid series, for cumole has been converted into 

 benzoic acid by Abel. 



The same chemist* has investigated the action of pentachlo- 

 ride of phosphorus on some fixed acids, which give rise to pyro- 

 genous acids. With mucic acid he obtained a chlorinated acid. 

 With pyromucic acid, he found that the action was the same as 

 with monobasic acids in general. Chloride of pyromucyle is 

 formed, a very highly refracting liquid boiling at 170° C, of a 

 similar odour to chloride of benzoyle, and which strongly excites 



^^CioH^O^ -t- PCP = PO^CP -j-HCl + C»<'H3C104. 



Pyromucic acid. Oxy chloride of Chloride of 



phosjjhorus. pyromucyle. 



Chloride of 'pyromucyle gives with water, pyi'omucic acid; 

 and with ammonia, pyromucamide, 



CIO H3 CIO" + NH3 = HCl -j- CioH^NO". 

 Chloride of pyromucyle. Pyromucamide. 



With maUc acid Bodart obtained an acid not containing chlo- 

 rine, and which appeared to be maleic or fumaric acid. 



* Comptes Rendus, Adjust 18, 1866. 



