— 95 — 
Semmler has taken up the study of these compounds which 
hitherto had not been examined further, and he has thereby found 
that the product obtained with sulphuric acid is an oxide, as it is not 
attacked by potassium and sodium at the boiling temperature. Its 
constants are: boiling point at 20 mm 95°, specific gravity 0,9647, 
index of refraction 1,4844, molecular refraction 45,2 (calculated 45,22 
for the oxide QoH^gO with one double linking). 
The dihydrocarvoxide (as the author designated this oxide) yields 
with bromine a fairly unstable dibromide of the melting point 55°; 
it is therefore unsaturated. On oxidation with a solution of potassium 
permanganate, an indifferent body CgH^gOg is obtained which melts 
at 58° to 59°, and has the boiling point 144° to 145° (at 13 mm) 
and the specific gravity 1,0351 (at 20°). This is identic with the 
alcohol C9 H^g O2 of the constitution 
/CH,— CH(OH)x 
CHo — CO — CH< >CH — CH3. 
^CH^ CH/ 
which Tiemann and Semmler^) had obtained direct from the 
dihydrocarveol -glycerine by oxidation. 
From this the author deduces for the dihydrocarvoxide the formula 
1 0-, 
C H ^ / C H« — C H \ 
■>C — CH<^ ^'CH — CH3 
C Hg C H2 — C H2 
The reactions further described also agree with this formula. 
If the oxide is submitted to the action of hydroxylamine in al- 
coholic solution, there is obtained the basic addition-product Cj^o H^^^ NOg 
of the melting point 113° to 114°, which dissolves readily in dilute 
acids, and which is reconverted by the latter with great facility into 
the oxide. 
The hydrochloride of the base melts at 93*^, and its benzoyl compound 
CjQHj^gN02(COCgH5) at 144°. From the formation of the latter 
the author concludes that a hydroxyl-group is present. 
If the base is heated in a tube for half an hour with alcoholic 
potassa to 160^, an alcohohc acid C^^QH-j^gOg is obtained in addition 
to nitril. This acid is monobasic, yields with carbanil a urethane, 
and can be oxidised into the ketonic acid Cj^oH^^gOg, whose semi- 
carbazone melts at 178° to 179°. If the alcoholic acid is heated 
with bromine water in a melting tube, an isomeric cumic acid is 
^) Berliner Berichte 28 (1895), 241. 
