— 47 — 



analysis of the semicarbazone shows that the formula C 10 H 16 O belongs 

 to the aldehyde. 



0,1687 gm. of the substance: 0,3906 gm. C0 2 , 0,1383 gm. H 2 0. 

 Found: Calculated for C n H 19 N 3 0: 



C 63,15 % 63,16 % 



H 9,11 % 9>o9% 



The content of this aldehyde (isomeric with citral) may possibly not 

 exceed 0,2 °/ of the oil. The quantity which we had in hand was 

 obtained from a large quantity of oil, and amounted to about 95 gm. 

 The aldehyde can be reduced with comparative ease to the corresponding 

 alcohol, by means of zinc dust and glacial acetic acid. The yield is 

 about 4O°/ . Less readily proceeds the reduction with sodium amalgam 

 in a weak acid solution. The acetate resulting from the zinc dust 

 reduction is a liquid with a fruit-like odour, which boils at 98°to 102 

 (4 mm. pressure). From the acetic ester, the alcohol was obtained by 

 saponification with alcoholic potash. It is a somewhat thick oil, rather 

 difficult to volatilise with water vapours, of a pleasant, peculiar odour, 

 and shows the following physical constants: 



boiling point 89 to 9 1 ° (4 mm. pressure), 236°to238°(755 mm. pressure) ; 

 di 5 o 0,9419; a D +o°; n D22 o 1,48652. 



With phenyl isocyanate it forms a phenyl urethane of the melting 

 point ioo° to 101 , which crystallises from dilute alcohol in leaflets. 

 The analysis of this derivative shows that the alcohol has the formula 



C 10 H 18 O: 



0,1613 gm. of the substance: 0,4403 gm. C0 2 , 0,1226 gm. H 2 0. 

 Found: Calculated for C 17 H 23 N0 2 : 



C 74,46% 74,70 % 



H 8,44 % 8,44 % 



This body is very stable towards strong formic acid at high 

 temperatures. 



The aldehyde C 10 H 16 O discussed above, when left standing exposed 

 to the air, readily oxidises into a leafy-crystalline acid C 10 H 16 O 2 . This 

 conversion proceeds more rapidly on treatment with moist silver oxide. 

 The acid crystallising from petroleum ether or dilute alcohol melts at 

 106° to 107 , boils at 133 to 135 (4 mm. pressure), and is identic 

 with the acid which had already previously 1 ) been isolated by us from 

 the saponification liquors of the oil. 



Analysis: 0,1795 gm. of the subst: 0,4706 gm. C0 2 , °> I 544 g m - H 2 0. 

 Found: Calculated for C 10 H 16 O 2 : 



C 71,50% 71,43% 



H 9,56% 9,52% 



A ) Report April 1904, 69. 



