— 70 — 
separated by repeated careful fractional distillation into the following 
fractions : 
I. 
Boiling point 
185- 
-193°; 
spec. 
gravity 0,8599; 
ajy — 
2^ 14'; 
1-38'; 
2. 
?) 
193 — 
-195°; 
J) 
„ 0,8621; 
3. 
j> )) 
195 — 
-198°; 
>) 
„ 0,8640; 
ajy — 
3^36'; 
4° 8'; 
4- 
?j 
198— 
-200^; 
jj 
„ 0,8680; 
aj) — 
5- 
i1 7? 
200 — 
-202°; 
7> 
0,8712; 
aj) — 
3° 14'. 
From every one of the above fractions the same phenyl urethane 
was obtained, which was done in the following manner: a mixture of 
2 to 3 g of the oil with a little more than the calculated quantity of 
phenyl isocyanate, was left standing for 3 to 4 days at ordinary tem- 
perature, at first w^ell-closed, subsequently with admission of air. As 
soon as the pungent odour of carbanil had completely disappeared, 
which occurred after 2 to 3 days, the crystalline mass, which still con- 
tained small quantities of oil, was boiled repeatedly with petroleum ether, 
which resulted in a separation of the phenyl urethane formed, from 
the diphenyl urea formed at the same time. We then exposed the 
solution of petroleum ether in a flat dish to spontaneous evaporation, 
when a very gradual separation of long needle-shaped crystals took 
place. The crystals dried on tiles showed the above-mentioned melting 
point after repeated recrystallisation from dilute alcohol. 
Two analyses gave values which point to the phenyl urethane of 
an alcohol C^oH^gO. 
1. o,i420g of the substance yielded 0,1081 g H2 O and 0,3877 g COg. 
2. o,i350g of the substance yielded 0,1025 g H2O and 0,3680 g COg. 
Found : Calculated for Hgg N : 
I. 2. 
C— 74,46 74,35 per, cent. 0=74,70 per cent. 
H= 8,46 8,44 „ „ H=: 8,44 „ 
As the separation of the phenyl urethane had been much delayed 
by the admixture of oil, we modified the method indicated, in this 
way, that the reaction mixture was left standing for about a week in 
a well-closed vessel, and was then immediately brought in contact with 
water. The slight admixture of oil was next removed from the mixture 
of crystals by means of steam distillation. The crystalline mass, dried 
on tiles, was treated further in the manner already indicated. The 
crystallisation was now completed very rapidly. In an attempt to 
regenerate the corresponding alcohol from the phenyl urethane, by 
prolonged boiling with a 20 per cent potash liquor, we obtained a bright 
yellow laevorotatory oil, which had the odour and boiling point of 
linalol, and which yielded citral on oxidation with chromic acid mixture. 
As, after this observation, there were reasons to assume that the 
urethane of the melting point 65° which was under consideration, was 
