164 A. R, PENFOLD. 
signment gave 20% boiling below 60° O.; 10% between 60 — 
120°C.; 30% at L23—133°C. and 297% at 140-—157° CO. 
Determination of the Terpene.—The fractions boiling 
below 60° C. at 10 mm. on redistillation at 765 mm. were 
found to consist almost entirely of d«pinene with a small 
amount of cineol. On removal of the latter by means of 
resorcin solution, the greater portion boiled at 155-157 O. — 
and had a specific gravity at 72° C. 0°8637, optical rotation 
+32°65°, and refractive index 20° OC. 1°4665. On mixing 
with an equal volume of I @ pinene (a@)»p 20° — 50°18" a copious. 
yield of nitrosochloride was obtained, which on purification 
melted and decomposed at 109° O. 
Its identity with d« pinene was confirmed by the pre- 
paration of pinonic acid:—116 ccs. were shaken with two. 
litres of 12% potassium permanganate solution and one kilo 
of ice for several hours, when the reaction was completed. 
After removal of manganese sludge the liquid was steam 
distilled to remove unchanged terpene and evaporated to a. 
small bulk. It was then acidulated with dilute sulphuric 
acid and the acid extracted with chloroform. On removal 
of the solvent, the liquid acid was distilled under reduced 
pressure. It boiled at 188-—192° O. at 15-16 mm., and 
became semi-solid on standing overnight at room temper- 
ature. The crystals were separated and purified. They 
melted at 68° O. and gave a semicarbazone melting at 207°C.. 
0°4064 gram in 10 cc. CHCl; gave (a)p 20° c. + 92°27". 
The terpene is ‘therefore, do pinene. 
Determination of Cineol.—This constituent was re- | 
covered from the resorcin solution (see above) by steam 
distillation, when it was obtained in very small amount. 
Its identity was established by its behaviour with phos- 
phoric acid and the preparation of the iodol derivative 
which melted at,111—112° O. 

