90 REPORT OF SCHIMMEL & Co. OCTOBER 1914/ APRIL 1915. am 
Linalool. Some years ago, Enklaar*) obtained 2,6-dimetyloctanol-6 in addition 
to 2,6-dimethyloctane, when reducing linalool with nickel and hydrogen, which speaks 
in favour of the formula for linalool, established by Tiemann and Semimler. P. Barbier — 
and R. Locquin’) feared that molecular transpositions might occur during the reduction 
with nickel and hydrogen. They therefore reduced linalool with platinum and hydrogen, — 
which process goes on at a low temperature. They used linalool obtained from linaloe 
oil by fractionated distillation and which showed the following constants: b.p. 87 to 
89° (13 mm.); d$> 0,888; [¢]p1z0 — 14,5°. 2,6-dimethyloctanol-6 was obtained as product 
of the reaction. It easily splits off water, forming 2,6-dimethyloctene-6,7, and is iden- 
tical with the 2,6-dimethyloctanol-6, which Barbier and Locquin prepared from methyl- 
isohexylketone and magnesium ethyl bromide. Enklaar likewise obtained the alcohol 
synthetically, but he started from methylheptenone, which according to Barbier and 
Locquin is easily disposed to undergo molecular transpositions when treated with 
magnesium alkyl haloids. Tetrahydrolinalool, obtained by reduction from linalool, boiled 
at from 86 to 88° (10 mm.) and showed [e¢], — 0° 24’. The allophanate of this tetra- 
hydrolinalool melted at 88°; the synthetical product, at 110 to 111°. The authors 
explain this difference as regards the melting point by the small refraction of tetra- 
hydrolinalool. The allophanate of tetrahydrolinalool, which was obtained by reduction 
of 3 i-linalool, melted likewise at 110 to 111°. ; 
Methylcyclohexanol. Following up his former papers on synthetic glucosides %), 
J. Hamalainen*) reports on the preparation of glucosides from isomeric methyl cyclo- 
hexanols by shaking the corresponding alcohol in ether with @-acetobromoglucose and 
silver carbonate, and saponifying the resulting acetyl compound. The yield is con-— 
siderably increased, if the acetobromoglucose is added in portions of 1 g. twice daily 
during the shaking, which is continued for several days. 
Borneol. About three years ago, J. Aloy and V. Brustier®) found that when con- 
ducting borneol vapours over copper oxide, heated to 250 to 300°, camphor results, and 
that at from 420 to 430° a mixture of terpenes is formed. As they now communicate‘), the 
dehydration likewise succeeds with other metallic oxides, which are not easily redu- 
cible, best. with thorium oxide. They give particulars regarding the terpenes formed: 
the reduction with thorium oxide at 350° yields a liquid of a terpene-like odour and 
boiling at between 150 and 180°; dsoo0 0,8637; @ + 1° 46’; np». 1,472. Three quarters | 
of this product consist of pinene: b. p. 156 to 160°; deoo 0,871; np»o 1,472. The authors 
did not prepare any derivatives of this pinene. The mixture of hydrocarbons, obtained ; 
from borneol with the aid of copper, had a similar composition. 
In the conversion of borneol into camphene, a thorough change in the whole ring 
system takes place when the water is split off. As borneol may be considered to be — 
a bicyclic pinacolin alcohol, it seems that the transposition, which takes place during 
the conversion into camphene, is closely connected with the rearrangement of atoms, 
observed when pinacolin alcohol is converted into tetramethylethylene. Already 
Wagner had, at the time, drawn a parallel between the formation of camphene from 
borneol and the conversion of pinacolin alcohol into -tetramethylethylene. In order 
1) Comp. Report April 1909, 125. — °) Compt. rend. 158 (1914), 1554. —. 8) Comp. Report October 1918, 
138. — 4) Biochem. Zeitschr. 61 (1914), 1; Chem. Zentralbl. 1914, I. 1887. — 5) Bull. Soc. chim. lV. 9 7335 
Report October 1911, 141. — &) Journ. de Pharm. et Chim. VII. 10 (1914), 49. 
