— 77 — 



It boiled at atmospheric pressure between 160 and 190 . The portion 

 boiling between 160 and 170 contained furfurol (red coloration with 

 a solution of aniline hydrochloride in aniline). The odour and other 

 properties of one of the next higher-boiling fractions of the b. p. 171 

 to 1 73°, pointed to the presence of a terpene, which, however, 

 could not be identified further (di 5 o 0,8611; « D -\- io° 40'). 



A fraction boiling about 6o° (5 mm. pressure) yielded in small 

 quantity a semicarbazone melting at 100 to 10 1°, which on heating 

 with dilute acid gave off the characteristic orange-like odour peculiar to 

 decylic aldehyde. A fall in the melting point of a mixture of this 

 semicarbazone and n-decylic aldehyde semicarbazone of the m. p. 102° 

 did not take place. The presence of n-decylic aldehyde is 

 thus proved. 



The portions boiling between 65 and 90 (4 mm. pressure) re- 

 acted with sodium bisulphite, with separation of a slimy bisulphite 

 compound. The aldehyde (2 1 / 2 g.) regenerated from the pure com- 

 pound distilled at 8o° (5 mm. pressure) and possessed the odour 

 peculiar to the higher fatty aldehydes, which, however, reminded at 

 the same time of cuminic aldehyde. Its semicarbazone crystallising 

 from dilute alcohol or benzene in brilliant leaflets with a greasy feeling, 

 melted at 167 to 168 , and on elementary analysis gave values which 

 point to the semicarbazone of a nonylic aldehyde: — 



0,1620 g. subst: 0,3547 g. C0 2 , 0,1513 g. H 2 0. 

 Found: Calculated for C 10 H 21 N 3 O: 



C 59,71% 60,30 % 



H 10,38% 10,55% 



The molecular weight, determined by Beckmann's method of 

 lowering the freezing point in benzene, was, in agreement with the 

 above formula, found to be 192,5 (calculated 199). Oxidation of the 

 aldehyde with moist silver oxide, which took place on the water bath 

 with decrepitation, yielded an oily acid with a smell like fatty acid, 

 which at highly reduced temperature solidified to leafy crystals, but again 

 melted slightly above o°. It boiled at 12 8° (4 mm. pressure), at atmo- 

 spheric pressure at 253 to 254 . Its silver salt, very unstable in the 

 light, was recrystallised from hot alcohol. 



0,2054 g. subst.: 0,3064 g. C0 2 , 0,1220 g. H 2 0. 

 0,2484 g. subst.: 0,0994 g. Ag. 



Found: Calculated for C 9 H 17 Ag0 2 : 

 C 40,68 % 40,75% 



H 6,60 <>/ 6,41% 



Ag 40,79% 40,75% 



