— 187 — 



Camphor. As a result of their investigations, G. L. Blanc and 



■. F. Thorpe 1 ) have found that when methyldiketo camphoric acid is reduced 



by Komppa's method, the methyl-group remains in combination with carbon ; 



from which it follows that their criticism of Komppa's camphoric acid 



synthesis is without foundation 2 ). 



Isocamphenilone. If, as is generally assumed to be the case, 

 camphenilone and fenchone are homologues, it would follow (as we gather 

 from a paper by Komppa) 3 ), that the hydrating of camphenilene (a hydro- 

 carbon which corresponds to camphenilone) would give rise to a new 

 alcohol, differing from camphenilol, and that oxidation of this alcohol 

 would yield a new ketone: ^ocamphenilone, analogous to the preparation 

 of isofenchyl alcohol from fenchene by Bertram and Helle. As a matter 

 of fact, Komppa, by hydrating camphenilene, obtained a new secondary 

 alcohol C9H15OH, isocamphenilol (b. p. 196° at 740 mm.), which he oxidised 

 into tsGcamphenilone, a ketone with a camphoraceous odour. The best 

 method of obtaining camphenilene is by heating camphenyl chloride with 

 aniline. It possesses the following constants: b. p. 140° (755mm.), d 20 o 0,8693. 



Zsofenchone. A good many years ago Bertram and Helle, working 

 in our laboratory 4 ) upon D-Z-fenchene, had prepared therefrom the i-iso- 

 fenchyl alcohol and from the latter, by oxidation, the ketone Ci Hi 6 O, 

 which was subsequently designated isofenchone by Wallach 5 ). The last- 

 named investigator, when oxidising isofenchone with permanganate of po- 

 tassium in alcoholic solution, obtained ^'sofenchocamphoric acid, in which 

 respect isofenchone is sharply differentiated from fenchone 6 ). Aschan 7 ) 

 has determined the constitution of this acid as follows: 1. The dibasic 

 acid is saturated; both v. Buyer's permanganate test and the bromine- 

 absorption test give negative results; ester-refraction normal. 2. The acid 

 shows a pronounced tendency towards the formation of anhydride. This 

 symptom, together with the fact that when the calcium salt is distilled 

 it does not afford a simple cyclic ketone, indicate a cyclically substituted 

 cis-glutaric or succinic acid. 3. The fact that the acid, when heated with 

 a mixture of glacial acetic and hydrochloric acids, is partially conver- 

 tible into a geometrically isomeric form, viz., trans-isofencho camphoric 

 acid (m. p. 169 to 170,5°), shows that the carboxyl which plays a part in 

 the conversion-process is linked directly with the carbon. 4. The as-acid, 



^ !) journ. chem. Soc. 99 (1911), 2010; Bull. Soc. chim. IV. 9 (1911), 1068. 



2 ) Comp. Report October 1909, 198; April 1910, 178; October 1910, 196; April 1911, 182; 

 October 1911, 147. 



3 ) Liebigs Annalen 387 (1912), 293. 



4 ) Journ. f. prakt. Chem. II. 61 (1900), 293; Report April 1900, 56. 



5 ) Comp. Report April 1908, 179. 



6 ) Comp. Report April 1908, 179; November 1908, 190. 

 : ) Liebig's Annalen 387 (1912), 1. 



