— 57 — 
1. Boiling point 194 — 196°; spec, gravity 0,8704; aj) — 5^48'; 
2. „ „ 196—197°; „ „ 0,8711; aD — 8^30'; 
3. „ „ 197—198°; „ „ 0,8701; ao — 8° 12'; 
4. „ „ 198—199°; „ „ 0,8699; ao — 8° 15'; 
5. „ „ 199—200°; „ „ 0,8714; ao — 7''5i'- 
All these fractions yielded with phenyl isocyanate, after standing 
for a long time, a phenyl urethane which melted in the pure state 
at 65°, and which had the same properties and behaviour as that 
described under petitgrain oil. The analysis gave values corresponding 
to the formula Cj^^ H23 O2 N, i. e. the phenyl urethane of an alcohol 
O H. 
0,1088 g of the substance yielded 0,0820 g Hg O and 0,2974 g CO2. 
Found: Calculated for Cj^7H23 02 N: 
C = 74,55 per cent 74,70 per cent 
H= 8,37 „ „ 8,44 „ 
The same phenyl urethane was also obtained from higher unsaponified 
fractions (boiling point 88 to 93° at 7 to 8 mm, saponification number 
126,3; 93 to 97° at 7 to 8 mm, saponification number 139,1). 
In a saponified fraction of the boiling point 74 to 77° at 8 mm 
pressure, (boiling point before saponification 94 to 98°, at 7 to 8 mm 
pressure) the alcohol was also detected. For the rest we refer to 
what is said under petitgrain oil. 
d-Terpineol of the melting point 35°. The high-boiling 
portions w^hich come under consideration for this body, were com- 
paratively rich in methyl anthranilate ; they were first of all treated 
with dilute sulphuric acid for the purpose of removing this ester. The 
fractions thus treated distilled between 90 and 114°, at 7 mm pressure, 
and showed only a slight fluorescence. The portion collected between 
90 and 95° was once more carefully fractionated at ordinary pressure. 
Between 215 and 220° an oil passed over which had a terpineol-like 
odour, and which on cooling first became viscid, and finally congealed 
when a terpineol crystal was introduced. The specific gravity of this 
fraction was o,Qi2. The pure white crystals melted above 33°. From 
the fraction mixed with phenyl isocyanate, which was dextrorotatory 
and contained terpineol, terpinyl phenyl urethane of the melting 
point 110° crystallised out. After recrystallisation from alcohol the 
melting point increased to 112°, 
This proves the presence in neroli oil of d-terpineol of the melting 
point 35°, and that as such, and not in the form of ester. 
Several years ago, A. Hesse^) made the assertion that oil of 
orange flowers contains indol, without however having produced up 
^) Berliner Berichte 32 (1899), 2612. 
