— 149 — 



(b. p. 82 ° [io mm. pressure]; (I150 0,9128), and methyl - 1 - isopropyl- 

 3 -cyclohexanone -4 (m - menthanone - 4) 



CH 2 C H.CH(CH 3 ) 2 



CH, • CH / ^CO 



CH 2 CH 2 



(b. p. 195 ; d^o 0,8914), whose oxime melts at 105 . 



In conjunction with G. Kayser, A. Kotz 1 ) has also worked on 

 the production of systems with two nuclei, in which one benzene 

 nucleus occurs combined with one hydrated benzene nucleus, 

 or two hydrated benzene nuclei combined indirectly. By 

 the action of benzyl chloride on methyl- i-cyclohexanone-3-carboxylic 

 ester- 4, with the use of sodium ethylate, there was formed methyl - 

 I -benzyl -4 -cyclohexanone- 3 -carboxylic ester, which was obtained 

 by distillation at 194 (12 mm. pressure); its semicarbazone melts 

 at 1 69° By boiling the ester with methyl alcoholic potash liquor, 

 methyl- 1 -benzyl-4-cyclohexanone-3 is formed, which is driven off by 

 water vapour under pressure. Its boiling point lies at 173 (13 mm. 

 pressure), at 166 (10 mm. pressure), its semicarbazone melts at 

 1 7 2° and its oxime at 13 9 . If to a mixture of the original product 

 and sodium ethylate, p-nitrobenzylchloride is added, there is obtained 

 methyl - 1 - p - nitrobenzyl - 4 - cyclohexanone - 3 - carboxylic ester-4, melting 

 at 90,5°. For the production of dimethyl- 1,1 '-trimethylene-4 -dicyclo- 

 hexanone-3,3 / -dicarboxylic ester-4, 4', trimethylene bromide is introduced 

 under otherwise analogous conditions into the reaction-mixture. The 

 ester boils at 257 to 263 (18 mm. pressure) and can be converted 

 with methyl alcoholic potash into the corresponding ketone, whose 

 semicarbazone melts at 107 . The oil regenerated from the latter 

 with sulphuric acid melts at 204 . The formulae of the bodies des- 

 cribed are as follows: — 



CHCH 3 

 NcH, HC 



H 9 C 



J CO HC 



C CH 



CH CH.CH 3 



CH H 9 c/\ciL 



CH.CH 3 



H 9 c/\CH 9 



CH H 2 C v 1 CO OC x .CHL 



C-CH 2 -CH 2 -CH 2 -C 



methyl- 1 -benzyl-4-cyclohexanone-3- 

 carboxylic ester-4 



dimethyl- 1, i'-trimethylene-4-dicyclo- 

 hexanone-3, 3 / -dicarboxylic ester-4,4' 



x ) Ibidem 348 (1906), 97. 



