201 



hydro-camphoceenic and dihydro-fencholenic acid lies in one of these 

 bodies possessing one methyl-group more. If, therefore, the hydrogen 

 atom which occupies the a-position towards the carboxyl group were 

 replaced by the methyl-group according to Haller's and Bauer's method, 

 dihydro-fencholenic acid should result. 



With this object in view the authors converted dihydro-campho- 

 ceenic acid into the chloride, a colourless liquid, boiling at 9 8° (16 mm.) 

 which was condensed with benzene in the presence of chloride of 

 aluminium into 3 -benzoyl- 1 -w<?propy 1-cyclopentane (b. p. i66°at 12 mm.; 

 oxime, m. p. 12 8°) which, after methylation by heating it with sodium 

 amide in the presence of toluene was split up into benzene and in the 

 amide of 3 - methyl - 1 - zlwpropylcyclopentane - 3 - carboxylic acid. This 

 synthetic amide must be identical with the racemic dihydrofencholenic 

 acid amide. It agreed, in fact, with that body, except as regards the 

 m. p., which was about 109 , while that of racemic dihydrofencholenic 

 acid amide is about n 6°, or, according to Barbier and Grignard, 

 from 114 to 1 1 5 . 



HX 



H C 



ch-ch/ 01 * 3 



X CH 3 



CH, 



JCH-COOH 



HX 



HX 



CH-CH<f CH 3 



X CH 3 

 CH 



c/ COC 6 H 5 

 N CH, 



HX 



HX 



CH-CH 



CH 9 



/CH 3 

 XH a 



Dihydrocamphoceenic 

 acid 



3-Benzoyl-3 -methyl- 1 - 

 z'sopropylcyclopentane 



c /CONE 2 

 X CH Q 



3 -Methyl- 1 -z'^propylcylo 

 pentane-3 -carbamide 



The authors, at first believing the product to be impure, repeated 

 their experiments, but without achieving any different result. They 

 therefore began to suspect that the amide which they had obtained 

 was an inseparable mixture of the as- and /^^-modifications. In 

 fact, further investigation showed that the synthetic amide contains 

 racemic amide. The action of sodium hypobromite upon dihydro- 

 fencholene amide from natural fenchone (placed at the author's 

 service by us), resulted in a symmetrical urea, diapofenchyl-urea, 

 m. p. 1 68°; the racemic amide obtained by mixing the two active 

 amides yielded two isomeric ureas, m. p. 175 and 161 , the syn- 

 thetic amide yielded of the bodies m. p. 162 to 163 and 13 6°. 

 The enantiomorphic ureas prepared from d- and 1-fenchone melted 

 at 1 68°; when mixed they yielded a racemic urea, m. p. 185 . This 

 latter was sparingly soluble and when re-congealed melted at 1 75°. The 

 racemic urea, when heated to 180 to 200 , underwent no outward 

 change, but it then became possible to decompose it by fractional 

 crystallisation from ether into two isomerides, melting at 162 to 163 

 and at 148 . It was also found possible to separate the mixture of 

 ureas which had its origin in the racemic acids, after heating, by 



