b.p. 



d. 



n D 



215 to 216° 



0,899 



1,4563 



211 „ 212° 



0,8865 



1,4466 



220° 



0,904 



1,4636 



220 „ 221° 



0,904 



1,4554 



184 



Methyl- \-isopropy\-5-cyclohexano\-2 

 Methyl- l-isopropyl-5-cycZohexanone-2 

 Tetrahydrocarveol 

 Tetrahydrocarvone 



Here also the b. p. and density of the bodies of the m-series are somewhat 

 lower then those of the p-series. 



Fenchone. Wallach 1 ) stated some time ago that the hydrocarbon 

 C 9 Hi 6 2 ), which is formed by splitting off ammonia from fenchylamine 

 hydrochloride is not a uniform body, notwithstanding that, judged by its 

 physical properties, it would appear to be so. When chemically examined, 

 however, the body proved to be an inseparable mixture of isomerous 

 hydrocarbons. When oxidised with permanganate of potassium in a 2% 

 cold aqueous solution, f- and 1-a-isopropylglutaric acid were obtained as 

 decomposition-products. The formation of these bodies was to be expected 

 if the original material contained A h - and A x -vc\ ethyl- \-isopropy\-3-cyclo- 

 pentene [(I) or (II)]. 



Wallach also reports on the nitrosochloride from the hydrocarbon 

 C 9 Hi 6 , from which, by recrystallisation , a fraction melting at 115° was 

 obtainable (m. p. of. the chemically pure nitrolpiperidine 160 to 161°). 

 In his endeavours to prepare an unsaturated ketone from this nitroso- 

 chloride the author encountered extraordinary difficulties. He has now 

 successfully tried another method, consisting in the reduction of the 

 nitrosochlorides in glacial acetic acid solution with zinc; but is true that 

 bases are simultaneously formed in this process. Wallach dissolved 30 g. 

 nitrosochloride by the cold method in glacial acetic acid and gradually 

 introduced into the solution about 50 g. zinc dust, finally concluding the 

 reaction by heating on the wather-bath. But the ketone which was driven 

 over with the steam was no more uniform than was the original material, 

 the hydrocarbon. The semicarbazone was split up into two parts, of which 

 the fraction with the higher m. p. (197 to 198°), when regenerated, yielded 

 a ketone which was identical with dihydropulegenone (III) (dihydrocamphor- 



*) Liebigs Annalen 379 (1911), 182. 



2 ) Wallach, Liebigs Annalen 369 (1909), 63; Report April 1910, 182; also comp. the in- 

 vestigations of Bouveault and Levallois, Bull. Soc. chim. IV. 7 (1910), 542, 683, 736, 807; 

 Report October 1910, 198. As Wallach observes, Bouveault and Levallois appear to have 

 "remained unacquainted with the German work", or they might have avoided a series of errors. 

 It is also singular that Bouveault and Levallois claim as a new discovery of their own the 

 detection of the presence of camphor in fenchone from fennel oil [Bull. Soc. chim. IV. 7 

 (1910), 546], whereas this occurrence has been made known by Wallach as far back as 1907 

 [Liebigs Annalen 352 (1907), 214; Report October 1907, 159] and suggestions have repeatedly 

 been discussed in chemical literature how best to remove camphor from fenchone. 



