— 9i — 



Assuming that this view is correct, the acid C 9 H 16 4 , on dry 

 distillation of the calcium salt, should be converted into isopropyl- 

 i-pentanone-3, and the latter, on oxidation with chromic acid, yield 

 a- and /?-isopropylglutaric acids. The properties of the former are 

 well known. 



In order to carry out this experiment, 6 gm. acid were neutralised 

 with lime, well dried, and after mixing it with an equal weight of 

 soda lime, distilled from a glass retort. The distillate was shaken up 

 with semicarbazide solution, and the resulting semicarbazone repeatedly 

 recrystallised from alcohol; melting point 187 . 



0,1034 gm. of the substance: 0,2244 gm. C0 2 ; 0,0842 gm. H 2 0. 

 Found Calculated for C 9 H 17 N 3 



C 59,18% 59,o% 



H 9,05% 9,3% 



The ketone regenerated from the semicarbazone by boiling with 

 10% sulphuric acid, boils at 190 to 193 , and possesses an extre- 

 mely powerful odour reminding of menthone and thujone. 



The oxidation of the ketone C 8 H 14 into the two isomeric glutaric 

 acids C 8 H 14 4 was accomplished with Beckmann's mixture. The 

 acids abstracted from the oxidation liquid with ether, could unfortunately 

 not be obtained up to the present in crystalline form and identified 

 by these means. 



The portions of waterfennel oil which did not react with sodium 

 bisulphite, were first saponified and then submitted to fractional 

 distillation in vacuo. The bulk passed over from 6o° to 145 (5 to 

 6 mm. pressure). In the residue there remained a considerable quan- 

 tity of resin. From the low-boiling portions it was possible to isolate, 

 by repeated careful fractionating, an alcohol of the following physical 

 constants: boiling point 197 ° to 198 , d 15 o 0,858; « D — 7° IO '; 

 n D2o° I >4499 1 - The alcohol possesses in a high degree the charac- 

 teristic odour of waterfennel oil, and appears to be the principal 

 bearer of that odour. With carbanile we obtained a phenylurethane, 

 which after recrystallisation from alcohol melted at 42 to 43 °. 



I. 0,1002 gm. of the substance: 0,2717 gm. C0 2 ; 0,0838 gm. H 2 0. 

 II. 0,1208 gm. „ „ „ o,32,86gm. C0 2 ; 0,1032 gm. H 2 0. 



Found Calculated for C 17 H 25 2 N; for C 17 H 23 2 N 

 1. 11. 



C 73,8 74,2% 74,14 74,7% 



H 9,3 9,49% 9>°4 8,4% 



The alcohol accordingly appears to have the composition C 10 H 20 O, 

 and not to be known up to the present. On oxidising it, we were 

 unable to isolate either aldehydes or ketones. In agreement with its 



