I IO 



Pinocamphone, to which, on the strength of what has been said 

 above, the formula 



CH Q 



OC- 



•CH 



(CH 3 ) 2 C 

 CH CH 



■CH 



CH 



belongs, was identified by its dibromide (m. p. 118 to 119 ), and by 

 oxidation with chromic acid mixture or permanganate. In both cases 

 there is formed, besides a keto acid, a dibasic acid, both of which 

 have the same carbon-content as the crude material. The keto acid 

 Qo -^-16 3 (a-pinonic acid), regenerated from its semicarbazone 

 (m. p. 203 °), melted at 103 to 104 . The dibasic acid C 10 H 16 4 

 (m. p. 186 to 1 8 7 ), isomeric with camphoric acid, was identified among 

 others by its silver salt. The process pinocamphone — > a-pinonic acid 

 (or the dicarboxylic acid) is explained by the following graphic formulae: 



I. 



CH 3 CH 3 



= C — I CH CH HOOC CO CH 



(CH 3 ) 2 C 

 I 

 CH 2 CH CH 2 



pinocamphone 



(CH 3 ) 2 C 

 I 

 CH 2 CH 



pinonic acid 



CH 



o = c- 



CH 8 



I 

 ■CH- 



•CH 



(CH 3 ) 2 C 



II. 



-> 



HOOC- 



CH Q 



-CH- 



(CH 3 ) 3 C 



CH 



CH 2 CH CH 2 



pinocamphone 



HOOC- 



-CH 



CH 9 



dicarboxylic acid 



The production of pinylamine has been greatly simplified by 

 Wallach in this manner, that he evaporates to dryness the lyes 

 formed in the reduction of nitrosopinene with zinc and acetic acid, 

 supersaturates them with lime in a copper still, and rectifies in vacuo 

 the pinylamine distilled with vapour. Further control - experiments 

 proved that as a matter of fact pinylamine is the base belonging to 

 carvopinone, for on oxidation with 1 per cent, potassium permanganate 

 solution it passes over directly into that ketone. 



