— I 9 I — 



recrystallised from dilute alcohol, formed lustrous needles possessing 

 the following properties: m. p. 57 to 58°, [a] D -}- 68,3° (in benzene); 

 very readily soluble in the usual organic solvents. When heated with 

 dilute sulphuric acid an oil with a clearly-defined odour of carvone 

 was obtained. The author proposes to distinguish the new carvoxime 

 as /J-carvoxime and the already known lsevorotatory body, m. p. J2°, 

 as a-carvoxime. 



Pulegone. So far, a series of observations on the properties 

 and behaviour of normal pulegone oxime have been available, from 

 which it is evident that the constitution of this body has been by no 

 means cleared up 1 ). Wallach, who had already previously reported 

 on normally-constituted pulegone oxime 2 ), has recently repeated his 

 experiments 3 ). He heated pulegone with hydroxylamine hydrochloride 

 in alkaline solution for 10 minutes, and from the mass resulting from 

 the reaction he obtained, by distillation in vacuo, three fractions, which 

 respectively proved to be acetoxime, methylcyclohexanone oxime and 

 pulegone oxime. The last-named body could only be purified with 

 difficulty; only after repeated recrystallisation from methyl alcohol was 

 the m. p. brought to 123 to 12 4 . Its specific rotatory power was 

 Md22° — 2 5^33° m a 6,43 per cent, solution of methyl alcohol. When 

 the oxime was boiled with diluted sulphuric acid a substance which 

 appeared to be pulegone was recovered from it. But as the semicarbazone 

 which was prepared from the pulegone, when recovered in different ex- 

 periments, did not possess a uniform m. p., decomposition with oxalic 

 acid was resorted to, and this process showed that the ketone recovered 

 was not pulegone, as had been accepted, but /^-pulegone. The semi- 

 carbazone of the /^-pulegone melted at 172 to 173 . The compound, 

 which has hitherto been regarded as pulegone - oxime is therefore 

 actually /w- pulegone oxime. 



CH 3 -/ \=C=(CH 3 ) 2 CH 3 -/ \_c/ 



II 3 



NOH NOH 



Pulegone oxime .Zwpulegone oxime 



In order to make a comparison iso- pulegone was prepared from 

 pulegone hydrobromide by Harries' process 4 ) and the oxime of this 

 was found to be identical with that from the pulegone referred to 

 above: m. p. 121 , Mdis — 26,20°. 



*) Report April 1897, 56; October 1898, 52. 



2 ) Liebigs Annalen 277 (1893), 160; 289 (1895), 347. 



2 ) Liebigs Annalen 3^5 (1909), 240. 



4 ) Berl. Berichte 32 (1899), 33°8; Report April 1900, 64. 



