— 126 



tained the above acids from fenchone, but with concentrated nitric acid, 

 whilst Wallach had had already before him dimethyl malonic acid, 

 formed by further oxidation of dimethyl tricarballylic acid. The con- 

 version of fenchone into m-cymene, discovered by Wallach, would 

 also be intelligible in accordance with Semmler's fenchone formula; 

 similarly, the relationship existing between camphor and fenchone, and 

 also the various well-known reactions of fenchone and its derivatives, 

 would find a better explanation by the new formula. In agreement 

 with the new formula are further the physical properties of fenchone, 

 and this is particularly evident if the properties of camphor and fenchone 

 are contrasted. 



According to this, camphor and fenchocamphorone on the 

 one side, and fenchone and camphenilone on the other, go 

 together. 



H C CH CH H 9 C CH CH, 



CK-C-CH, 



H C 



CH CO 



Fenchocamphorone 



H C 



H C 



CH C = (CH,) 2 



I 



CH 2 

 I 

 CH-^ — —CO 



CH 3 

 Fenchone 



Camphenilone 



Camphor would consequently be methylated fenchocamphorone, 

 and fenchone methylated camphenilone. 



Menthone. A. Kotz and L. Hesse 1 ) report on a synthesis of 

 menthone from methylhexanone. They condense methylhexanone 

 and ethyl oxalate by adding a strongly cooled mixture of ester 

 and ketone in small portions to a solution of sodium ethylate which 

 is kept cold. The temperature may thereby rise only slightly and 

 temporarily above that of the freezing mixture. After standing for 

 15 hours, the dark-brown reaction mixture is introduced into very 

 dilute sulphuric acid of o°; the oxalic ester of methylhexanone formed 



2 ) Liebig's Annalen 342 (1905), 306. 



