or 



153 — 



CH-C(CH 3 ) 2 



N —/ 



and it is formed in all cases in which, according to the previous 

 opinion, cyanomenthone is to be expected. The optical rotation of the 

 anhydramide in a 200 mm. tube was [a] D -j- 66,6° (in absolute alcohol). 



Fenchone. Jointly with K. Bartelt, F. W. Semmler 1 ) publishes 

 two papers on the determination of the constitution in iso- 

 meric fencholenic acids. The /?-acid is formed by saponification of the 

 corresponding nitrile, which can be produced from fenchone oxime. 

 The assumption that the reaction-mechanism proceeds in a manner 

 analogous to the production of a- and /?-campholenic nitrile from 

 camphor oxime, where the first-named nitrile can be converted in 

 the last-named, could not be upheld. On the contrary, the two 

 fencholenic nitriles are formed primarily alongside each other, and up 

 to the present it has not yet been possible to convert the one in 

 the other. 



^-Fencholenic acid forms a difficultly soluble silver salt, which 

 yields with methyl iodide a methyl ester C 9 H 15 «COOCH 3 (b. p. 97 

 to 99 ; d22° 0,9808; n D20 o 1,46459). The latter can be reduced with 

 sodium and alcohol to the corresponding alcohol C 10 H 18 O (b. p. 106 

 to 108 ; d 22 o 0,9272; n D20 o 1,48033). 



When /? -fencholenic acid is treated with concentrated sulphuric 

 acid, the corresponding lactone is formed, as already mentioned on 

 another page 2 ). This, when shaken with dilute soda liquor in the 

 cold, yields hydroxyhydrofencholenic acid C 10 H 18 O 3 of the m. p. no°. 



If /? - fencholenic acid is diluted with equal quantities of benzene 

 and water, and a powerful current of ozone is passed through the 

 mixture, a solid ketonic acid C 7 H 10 O 3 is formed; b. p. 166 to 170 

 (12 mm. pressure); di 6 o 1,1533; Mp-j" 13,15° (in 50 percent, alcoholic 

 solution); n D 1,472. Semicarbazone, m. p. 198 to 199°; oxime 

 m. p. 1 45 . When treated with permanganate in neutral or weak 

 alkaline solution, this ketonic acid is split up into a not yet identified 

 tricarboxylic acid C 7 H 10 6 very readily soluble in water, on whose 

 distillation in vacuo, with loss of carbonic acid, an acid passes over 

 which Semmler regards as a-methyl glutaric acid (b. p. 205 to 208 

 [12 mm. pressure]; m. p. 77 to 7 8°). 



The melting point of the /? -fencholenic acid which is formed 

 from the comparatively readily saponifyable /? -nitrile, is at 72 to 



*) BerL Berichte 39 (1906), 3960, and 40 (1907), 432. 

 *) See present Report p. 146. 



