4 
Indian Forest Records. 
[Vol. vni 
into the < -nitrol-piperide melting at 93-94° and the ^-nitrol-piperide 
melting at 110-111°. Judging from the somewhat low optical activity 
dipentene was probably also present in this fraction but it was not 
found possible to isolate any derivatives of this hydrocarbon. 
Fraction VI. 
This fraction which boiled above 180°/699mm. was refractionated 
under diminished pressure (60mm.) and the fraction boiling below 
150° collected separately. This fraction on distillation at the ordinary 
pressure (699mm.) was found to boil mainly between 200-240° and had 
the following constants, D f§-° 0*9203, N 3 ^ 0 1*4732, —29-03°. 
These constants indicated that the oil was probably a mixture of an 
alcohol and an ester. It was therefore hydrolysed with an excess of 
alcoholic potassium hydroxide solution and the resulting oil distilled 
when the main fraction passed over between 195-220°/697mm. This 
fraction consisted essentially of terpineol since it yielded a nitrosochloride 
melting at 112-113° which on treatment with piperidine gave a nitrol- 
piperide melting at 159-160.° In order to determine whether borneol 
was present the terpineol was converted into terpin hydrate by treat¬ 
ment with dilute sulphuric acid. A careful examination of the products 
of the reaction failed to reveal the presence of borneol. 
The alkaline solution from which the terpineol had been isolated 
was concentrated on the water bath when, on acidification with dilute 
sulphuric acid, a liquid acid separated. The acid was purified by dis¬ 
tillation in steam, in which it was slowly volatile, and fractionally con¬ 
verted into the silver salt. Three fractions were obtained which showed 
on analysis the following percentages of silver I. 39*8, II. 40-6, III. 42-1. 
Fractions I and II agree well for the silver salt of nonylic acid which 
requires Ag=40-7 per cent. These results indicate the presence of terpinyl 
nonylate in this fraction of the oil and the presence of this ester was 
confirmed by the isolation of terpinyl nonylate from the higher boiling 
fractions (see below). 
The fraction from which the terpineol and terpinyl nonylate had 
been separated and which boiled above 150°/60mm. was repeatedly 
refractionated when ultimately three main fractions were obtained 
(a) 140-145°/50mm., (b) 155-160°/50mm., (c) 180-190°/50mm. Fraction 
(a) consisted of nearly pure terpinyl nonylate since on analysis it gave 
the following figures :— 
0-1397 gave 0-4046 C0 2 and 0-1414 H 3 0 0=78-0, H=10-9. 
C 19 H 31 0 2 requires 0=77-5, H=ll-5 per cent. 
[ 371 ] 
