759 
The liquid was now treated with anhydrous sodium sulphate and 
again distilled in vacno. Further analysis of the product gave, 
however, no better results. (71.08 °/, C. and 12.59 °/, H). 
The unsaturated tea-alcohol forms with avidity an addition compound 
with bromine, as was previously shown. The quantity of bromine 
added. however, was smaller than is to be expected from a substance 
of the formula C,H,,O, being only 87°/, of that amount. 
Two fresh determinations gave the following results: 
I. 1.017 grm. of the alcohol in chloroform solution ‘cooled in 
ice-water add 1.363 grm. bromine. 
II. 0.529 grm. add 0.707 grm. : 
From these result it appears that only 83.2°/, and 83.5 °/, 
respectively of the calculated quantity of bromine is added. 
As I suspected that the unsaturated alcohol perhaps contained a 
hexyl alcohol as impurity, | attempted to purify a larger quantity 
of the bromine addition compound *) from this by heating in vacuo 
at 100°. A subsequent treatment with zine dust should give the 
hexylene alcohol in a pure state. Since, however, the bromine 
addition product gave hydrobromie acid, I was unable to carry out 
this intention. 
Treatment of the unsaturated alcohol with phenylisocyanate gave 
no crystallised product. On the other hand a-naphthylisocyanate gave 
an «-naphthylurethane (m. p. 76°), the melting point of which could 
be raised to 80° after repeated recrystallisation from petroleum ether. 
On treatment with phthalic anhydride, the tea alcohol gave a 
liquid acid ester of which the silver salt melted at 140°. 
Oxidation of the tea alcohol with potassium permanganate in 
neutral as well as in alkaline sodium carbonate solution, proceeds 
very smoothly. About 3 ¢.c. of acid were obtained from 11.5 grm. 
on treatment with 50 grm. potassium permanganate in 4 °/, solution, 
This acid, as before, had a smell resembling that of butyric acid. 
On distillation of the acid, however, the principal fraction, besides a 
small first fraction in which formic acid could be detected, was a 
liquid boiling between 125° and 145°, while the residue in the 
flask consisted of a liquid of higher boiling point with a smell of 
perspiration. The principal fraction, on redistillation, gave a liquid 
of boiling point 140°—145°; which on being boiled with water and 
calcium carbonate was transformed into a calcium salt which was 
found on analysis to contain 21.2°/, Ca. This result in conjunction 
with the boiling point of the acid obtained, show that the latter 
') This does not solidify in liquid ammonia 
