CH q 



CEL 



/ 

 NH 2 CO 



CH, 



CH Q 



>C — < 



pulegone amine 



— 125 — 

 NH-OH co 



-CH 9 



pulegone hydroxylamine V 



NH CO 



-CH Q 



CH, 



CH Q 



-C< 



-CH, 



NH 2 CHOH 



CH Q 



CH, 



base C 10 H l7 NO 



-CH Q 



tetrahydro base 



Menthone. For the production of alkyl- and alkylidene deriv- 

 atives of cyclic ketones, A. Haller 1 ) employed sodium amide instead 

 of sodium metal hitherto used for this reaction, and by these means he 

 prevented the formation of the corresponding alcohols which otherwise 

 occur as by-products. By allowing aldehydes or halogen alkyls to act 

 on the produced sodium compound of the ketone in question, the 

 desired products of condensation or substitution were obtained directly. 

 The alkyl menthones produced by Haller are colourless oils which, 

 with the exception of methylmenthone, all have a musty and menthone- 

 like odour. Up to the present the following bodies have been obtained: 



methylmenthone boiling point 96 to 97° (1 3 mm 



pressure) W D +2 0, 1 8° 



ethylmenthone „ 



„ IOI° „ I02°(l3 „ 



„ ) n +38° 



propylmenthone „ 



„ 128 ,, i32°(i9 „ 



„ ) „ +39,20° 



isobutylmeuthone „ 



„ I2 4 °„ I28°(lO „ 



„ ) „ +45° 



isoamylmenthone „ 



„ 138 ,, i43°(io „ 



„ ) „ +31,48° 



allylmenthone „ 



„ 134°,, i37°(20 „ 



» ) „ +25,42° 



The anomalies of the foregoing compounds, with regard to boiling 

 points and rotatory powers, which latter are all contrary to those of 

 the used menthone (Wd — 26,18°), may possible be attributed to the 

 sensitiveness of the ketone towards alkalis and the formation of several 

 stereo-isomerides. The synthesis will also be employed for camphor, 

 pulegone, thujone, etc. 



The menthone amine 2 ) to be obtained by nitration of the menthone 

 and subsequent reduction, yields on benzoylating two benzoyl-com- 



x ) Compt. rend. 138 (1904), 1139. 

 2 ) Chem. Centralbl. 1895, II, 1160. 



