CH,. 



I 

 C-CN 



H 2 C 



H,C 



JcH(CH 8 ) 2 



IV. fenchoiic acid nitrile. 



— 186 — 



H 3 C^ /OH 



C 

 H,CL 



J CH(CH 3 ) 2 



V. methyl-l-/sopropyl- 

 3-q/cZopentanol-l . 



H3CCCOOH 



H 2 c/\cH 2 



H 2 C 



C:C(CH 3 ) 2 



VI. ^-fencholenic acid. 



The researches by Bouveault and Levallois 1 ) into the constitution of 

 fenchone, upon which we commented some time ago, have now been 

 published elsewhere with full experimental details 2 ). 



Thujone. The Journal of the Chemical Society 2 ) contains a detailed 

 account of the investigations by Thomson 4 ) upon which we commented in 

 our last Report. 



On the reduction of thujone, see p. 165. 



Pulegone. In one of our previous Reports we described the experi- 

 ments in reduction which have been carried out by Skita 5 ) by the agency of 

 palladium chloride. Since then the author has continued his investigations 

 in collaboration with H. Ritter 6 ). The authors added to 10 g. d-pulegone 

 (from pennyroyal oil), 0,25 g. palladium chloride and 0,25 g. gum arabic and 

 into the aqueous solution of these substances, they pressed hydrogen at 

 1 atm. overpressure. In all, 1,8 1. hydrogen was absorbed. From the 

 reduction products the authors obtained a principal fraction with b. p. 

 206 to 207°, possessing the same constitution as menthone: d 20 o 0,889. 

 This body, which had an odour of peppermint, formed a liquid oxime and 

 had [«] D20 o + 11,7°. In addition to menthone, a little menthol (b. p. 210 to 

 211°) had been formed. 



It was further discovered that aldehydes and ketones are capable of 

 being reduced to alcohols, but to accomplish this it is necessary con- 

 siderably to raise the overpressure of the hydrogen. Thus when hydrogen 

 was forced into phenylacetic aldehyde at a pressure of 5 atmospheres, a 

 not inconsiderable quantity of phenyl ethylalcohol , b. p. 108 to 110°, di 8 o 

 1,038, was produced. 



*) Compt. rend. 148 (1909), 1399, 1524; Report October 1909, 200. 



2 ) Bull. Soc. chim. IV. 7 (1910), 963, 968. 



3 ) Journ. chem. Soc. 97 (1910), 1502. 



*) Proceed, chem. Soc. 97 (1910), 177; Report October 1910, 198. 

 3 ) Berl. Berichte 42 (1909), 1633; Report October 1909, 186. 

 «) Berl. Berichte 43 (1910), 3393. 



