jf lami Soe Ga Wh te iti too bts aks sia A Baa 
ER eo "Notes: ON. | SCIENTIFIC RESEARCH. Ba 15 
B exactly analgeons to the corresponding ally! denranves: the bromide was easily 
hy d: rca by water and easily added to tertiary bases, §c. Cinnamyl bromide showed 
‘the m.p. 31 to 32°. It may be assumed that cinnamyl chloride would readily pass 
~ over into cinnamyl mustard oil, as well as cinnamyl phenyl ether suffer Claisen’s 
real angement, both questions which the authors, at present, were unable to decide. 
Hydrocarbons. 
A new method for preparing some incarusated hydrocarbons. — B. T. Brooks and 
p- _ Humphrey?) examined the reactions passing off in the refining of petroleum distil- 
- Iates, such as are usually carried out in the petroleum refineries. It was. principally 
_ the question of the action of concentrated sulphuric acid on unsaturated aliphatic 
hydrocarbons, yet the authors describe, in addition, some reactions which are of 
- interest with regard to our special branch. For the preparation of hydrocarbons from 
_ secondary or tertiary alcohols they recommend distillation with iodine, this method 
- giving better yields than the other ones commonly used. Menthol, for instance, splits 
off water easily on slow distillation with addition of 1 per cent. iodine; a hydrocarbon 
‘is formed thereby (b.p. 169 to 170°, d= 0.811) which is probably identical with 
_ Wallach’s”) -menthene of the same boiling point. When 119 cc. of this hydrocarbon 
= are shaken with 100 cc. sulphuric acid of 85 per cent. strength dimenthene CooHse6 
(bz p. 310 to 315°; d 0.899; npe0o 1.4795) is formed with a yield of 55 per cent. The 
e ~ sulphuric acid contained an oil smelling of menthol, but no crystalline body could - 
be prepared therefrom. 
_- Furthermore, they studied the action of stilphirie acid on «- and 2 ainene limonene, — 
_ and myrcene. When sulphuric acid of 85 per cent. is added, at 0°, to «-pinene, the 
4 principal product is a dimeric substance CooHgo, b. p. 170 to 175° (15 mm.), in addition 
to a viscid trimeric body. When fractionating the first runnings a smell of borneol 
"was ‘noticed, but it was not possible to isolate a crystalline compound. On acting 
_ with a sulphuric acid of 72 per cent., at 25°, the dimeric hydrocarbon resulted in a 
yield of 62 per cent. §-Pinene, as well as limonene, behaved in the same manner. 
. In order to obtain myrcene, the authors heated 270 g. linalool for two hours with 
7. 3 g. iodine, when nearly the theoretical amount of water was split off. On frac- 
__tionating the reaction-mixture, they obtained 103 g. myrcene (b.p. 165 to 167°), 24 g. 
_ of a fraction b. p. 167 to 177°, evidently a mixture of myrcene and limonene, as well 
. as about 143 g. unattacked linalool and polymerization products. Myrcene reacted 
“so violently with sulphuric acid of 85 per cent. that oe ae cobain and 
oxidation could not be prevented. 
2 Styrene, when treated with sulphuric acid ot 85 per cent., gave rise solely to the 
_ tesinous polymeride, phenylethyl alcohol not being formed. 
i 
a Camphenilene. — Some years ago, S. V.. Hintikka and G. Komppa’®) described the 
| oo of camphenilone into isocamphenilone. Camphenilone was reduced to 
é. ia this alcohol transformed into camphenilyl chloride and the latter, by 
abstraction of hydrogen chloride, into camphenilene; from this hydrocarbon, by the 
us bal method, isocamphenilyl acetate, and by oxidizing the ee alcohol, zsocamphenilone 
was obtained. 
1) Journ. Amer. chem. Soc. 40 (1918), 822. — *) Liebig’s Ann. 800 (1898), 282. — 3) Liebig’s Ann. 887 
12), 293; Report April 1912, 187. 
8* 
