— 203 — 



chloroform solution to act upon it, the product of reaction, when 

 treated with bisulphite, was found to contain benzaldehyde. In 

 the portion which did not react with bisulphite, benzaldehyde was 

 found present as well as fenchone, the latter being identified from 

 the semicarbazone, m. p. 179 to 181 . From these data Leroide 

 concludes that the hydrocarbon which boils at 152 to 154 represents 

 benzal-hydrofenchene C 10 H 16 : CH • C 6 H 5 . 



Camphenilone. The formula originally given by Wagner 1 ) for 



this ketone 2 ) which appears in the process of oxidising camphene 



CH 9 CH, 



/ - \ 



CH — CH 2 — CH 



\ / 



CO C(CH 3 ) 2 



has subsequently been confirmed by Semmler 3 ) and others. Komppa 4 ) 

 has prepared a series of derivatives of this ketone (most of which 

 are new), by reducing camphenilone with sodium and alcohol to the 

 corresponding alcohol, camphenilol, m. p. 84 and converting the latter 

 into its acetate (b. p. 95 to 97 (17 mm.); d^- 0,9974; n r>2o° 1,4628; mol. 

 refr. determined 50,241, calculated for the saturated bicyclical com- 

 pound C u H 18 2 50,399); its phenyl urethane (needles of m. p. 99,5°) 

 and its acid phthalate (small crystals, m. p. 148,5 to 149 ). From 

 the oxime prepared from camphenilone according to Auwers' method 

 (the m. p. of which was found to be 105,5°) ^ was possible to 

 obtain, by reducing with sodium and absolute alcohol at water -bath 

 temperature, distilling by steam, neutralising the distillate with hydro- 

 chloric acid and evaporating to dryness, the hydrochloride of the un- 

 known camphenilyl amine 



,C H 2 — C H 2 

 CH — CH 2 — CH 

 \CH-C(CH 3 ) 2 

 NH 2 



in the shape of long, thick needles, readily soluble in ether and not 

 melting at 200°. As bye-product, the nitrile of camphoceenic acid was 

 formed, resulting from the action of the hydrochloric acid upon the 

 unchanged oxime; it could be separated from the amine hydrochloride 

 by steam distillation. The free base of the last-named body was liber- 

 ated by decomposing with an excess of 50 per cent, aqueous potash 



*) Chem. Zentralbl. 1897, I. 1056. 



2 ) Comp. Report October 1899, 62. 



8 ) Berl. Berichte 39 (1906), 2577; 42 (1909), 246; Report April 1909, 121. 



4 ) Liebig's Annalen 366 (1909), 71 (1st treatise). 



