- 78 - 



These figures also point to a nonylic acid. The zinc salt of the 

 acid regenerated from the silver salt melted at 127 to 12 8°, the 

 copper salt a little above 200 . The aldehyde in question is there- 

 fore a nonylic aldehyde, which on oxidation is converted to a 

 nonylic acid, whose properties and salts show a great resemblance to 

 those of pelargonic acid. 



An oil of the b. p. 73 to 7 5 (4 mm. pressure) isolated from the 

 non-aldehydic fractions by fractional distillation, separated off at a 

 low temperature abundant quantities of leafy crystals, which on closer 

 examination were found to be naphthalene. The rest of this com- 

 pound which had remained dissolved in the oil, was separated off in the 

 form of its picrate. This, after purification from alcohol, melted at 

 1 49 . From this the naphthalene was isolated by heating with soda 

 liquor and distilling in a current of steam. In this manner we ob- 

 tained about 4Y2 g- of the substance. The body purified partly by 

 sublimation, partly by crystallisation, melted at 80 to 80,5°, and on 

 analysis gave the values required for naphthalene: — ■ 



0,1703 g. subst: 0,5828 g. C0 2 , 0,0990 g. H 2 0. 



Found: Calculated for C 10 H 8 : 



C 93,33% 9375% 



H 6,46 % 6,25 o/ 



The napththoquinone produced by oxidation with chromic acid 

 in glacial acetic acid, melted at 125 . 



This occurrence of naphthalene is particularly interesting, as this 

 body had up to the present only been found in very isolated cases 

 as a constituent of essential oils. To our knowledge there is in the 

 literature only a short notice by v. So den and Rojahn 1 ) on the 

 detection of this hydrocarbon in the oils of clove stems and storax. 

 It is a remarkable fact that this body with such an unpleasant and 

 characteristic odour is present in a particularly delicate and pleasant 

 smelling essential oil. As on repeated treatment with picric acid at 

 raised temperature a very large portion of the oil resinified, the un- 

 changed oil was, after previous removal of any picric acid still dissolved 

 in it, freed from the resinous constituents by distillation with steam. 

 Attempts to identify an alcohol or a ketone in this oil boiling chiefly at 

 220 to 230 , were without result. 



We would still mention a semicarbazone of a ketone (m. p. 217 

 to 2 1 8°) isolated from a fraction of the b. p. 65 to 71 (4 mm. pressure) 

 which had not yet been treated with bisulphite. The ketone hat a 

 mint-like odour. 



x ) Pharm. Ztg. 47 (1902), 779; Report April 1903, 29. 



