18 Henry G. Smith: 



portion distilling below 158° had 



Specific gravity at 15° =0.8596. 

 Rotation aD= +21.2°. 

 Refractive index at 20° = 1.4569. 

 ;and formed a nitrosochloride, which melted at 104° C. 



The lower boiling constituent in the oil was thus shown to be 

 -dextrorotatory pinene. 



Possibly limonene Avas also present in the intermediate portion, 

 as the specific gravity was only 0.8590. 



The second, or large fracfion, gave the following results : — 

 Specific gravity at 15°C. = 1.0519. 

 Rotation aD= +0.4°. 

 Refractive index, at 20° = 1.5230. 

 "Soluble in 0.5 volume of 70 per cent, alcohol, remaining clear on 

 further addition. 



After removal of any phenol which might be present in this 

 fraction, it was again distilled under reduced pressure, the first 

 15 CO. being discarded. The remainder boiled fairly constant 

 at 191 °C. under 47 millimetres pressure. The product gave the 

 following results : — 



Specific gravity at 20°C. = 1.0705. 

 Inactive to polarised light. 

 Refractive index at 24°C = 1.5283. 

 It was thus considered that the bulk of the oil consisted of this 

 -constituent. When freshly distilled, it was practically colourless, 

 had a slight fluorescence, and a delicate aromatic odour, reminding 

 somewhat of linalool. It darkened slightly on keeping. 

 Analysis gave the following ; — 



(a) 0.1688 gram gave 0.1196 HoO; and 0.4222 CO^ : H = 7.87 



and C. 68.22 per cent. 



(b) 0.1332 gram gave 0.0932 H.O; and 0.3362 CO;^ ;H = 7.8 



and C. 68.85 per cent. 

 CiaHiA requires H. 7.75 and C. 69.1. 



Methoxy Detepmination. 



(a) 0.2872 gram gave 0.9498 Agl equal to 43.6% OCH3. 



(b) 0.3144 gram gave 0.9939 Agl equal to 41.8% OCH3. 



It is thus evident that the molecule Cj^HihOj contains three methoxy 

 groups. 



That the molecule was unsaturated was shown by the action of 

 Bromine, when the substance was dissolved in carbon tetrachloride. 



