201 



,0s 



Os 



III. CH 2 < >C 6 H 3 CH — CHCH 3 

 IV. 







CH 2 l —0 



V. 



O 

 CH 2 L 



CH(OCH 3 )CHBrCH 3 



CH (OCH 3 ) • CH(NH - CH 3 ) - CH 3 



Acids. 



Cyclogeranic acid. Some time ago we announced 1 ) that Bougault 

 had obtained l,5,5-trimethyl-#-c^cfohexenol (or -one) -2 from a-cyclogeranic 

 acid by means of oxidation with hypoiodous acid. The first-named body 

 may be very readily obtained, (as the author has recently discovered) 2 ), 

 by oxidising trimethyl q/c/ohexenol with mercuric acetate in a solution 

 of acetic acid. It is, however, necessary in the first instance to convert 

 the alcohol into its acetate, because free trimethyl q/cZohexenol is im- 

 mediately oxidised by mercuric acetate into trimethyl cyclohexenone. In 

 cases where it is desired to prepare the ketone, the easily-accomplished 

 oxidation with mercuric acetate is unquestionably to be preferred to that 

 with chromic acid mixture. 



When the nitrile of cyclogeranic acid is heated in an autoclave with 

 alcoholic potash to from 175 to 180°, no uniform saponification-product 

 is formed, but a mixture of two isomeric amides melting at 121 

 and 202° respectively 3 ). It follows that, as surmised by Bouveault 4 ), 

 cyclogeranic acid nitrile is not uniform, but consists of a mixture of 

 «- and ^-cyclogeranic acid nitriles, corresponding to «- and /?-ionone, 

 and that the amides melting at 121 and 201° are those of «- and 

 ^-cyclogeranic acid. In order to make sure on this point, Bouveault at- 

 tempted first to prepare «- and ^-cyclogeranic acid synthetically and 

 then to convert these bodies into their amides. The «-acid was obtained 

 by the following method: — The condensation of ethyl iodoacetate with 

 methyl heptenone yielded ethyl dihydroxy geraniate from which, by the 

 elimination of water, ethyl ester of geranic acid was obtained, which 

 was converted into the ethyl cycloger aniate. This ester was very difficult 

 to saponify; after 20 hours' heating to 110—120° in an autoclave with 



') Compt. rend. 150 (1910), 397; Report April 1910, 188. 



-) Compt. rend. 150 (1910), 534. 



3 ) Barbier and Bouveault, Bull. Soc. chim. III. 15 (1896), 1002. 



*) Ibidem IV. 7 (1910), 350. 



