— 148 — 



atom in the molecule is fairly mobile. Hot concentrated potash 

 solution hydroxylises the body to a-hydroxycyclohexanone 



CH 2 C H 2 



CH,/ NcO 



CH 2 CHOH 



which the authors designate as "adipoine". This body sublimes at 

 ioo° (ordinary pressure) and melts at 113 , its semicarbazone at 

 165 . Its constitution is shown, analogous to that of chlorocyclo- 

 hexanone, on oxidation with permanganate by the formation of 

 adipic acid. Grignard's salts condense with chlorocyclohexanone 

 according to the equation: — 



C H 2 C H 2 C H 2 C H 2 



CH 2 / ^CO + RMgCl = MgCl 2 + CH / ^>CO 



CH 2 CHC1 CH 2 CH— R 



In an analogous manner are produced: a-methylcyclohexanone, b. p. 6o° 

 (10 mm. pressure); semicarbazone, m. p. 195 ; a - ethyl cyclohexanone, 

 b. p. 65 (10 mm. pressure); semicarbazone m. p. 157 ; a-isopropyl- 

 cyclohexanone, b. p. 8o° (10 mm. pressure). 



In connection with the synthesis 1 ) of menthone from methyl- 3- 

 cyclohexanone already discussed by us, Kotz publishes jointly with 

 A. Mich els 2 ) a synthesis of m-menthanone-2 and m-menthanone-4 

 from methyl -1 -cyclohexanone- 2 and methyl- 1- cyclohexanone- 4. By 

 the action of oxalic ester on these cyclohexanones, the authors ob- 

 tained the corresponding ketone esters. Methyl -1 -cyclohexanone- 2- 

 oxalic acid ethyl ester-3 passed over, by splitting off carbonic oxide, 

 into methyl- 1 -cyclohexanone- 2 -carboxylic ethyl ester-3 boiling at 115 

 (12 mm. pressure), whose semicarbazone melts at 140 . Methyl- 

 1 - cyclohexanone - 4 - oxalic acid ethyl ester-3 yielded methyl - 1 - cyclo- 

 hexanone- 4 -carboxylic ethyl ester-3, b. p. no° (10 mm. pressure); 

 semicarbazone, m. p. 134 . By saponifying the bodies converted into 

 their isopropyl esters by means of sodium ethylate and isopropyl 

 iodide, and by splitting off carbon dioxide, the authors finally arrived 

 at methyl- 1 - isopropyl - 3 - cyclohexanone - 2 (m-menthanone - 2 ) 



CO C H.CH(CH 3 ) 2 



CH 8 .CH/ /CH 2 



ci^ CH, 



*) Liebig's Annalen 342 (1905), 306; Report April 1906, 126. 

 2 ) Liebig's Annalen 348 (1906), 91. 



