eae ee 
6 = a 
e 
7 _is easily volatile with steam, possesses an agreeable, camphor-like smell, but hhas not 
- been closely investigated as yet. 
a-Terpinene. In a treatise on dialkylcyclohexadienes and their carboxylic acids, 
_K. von Auwers and R. Hinterseber’) describe among other matter the preparation of 
e-terpinene (1-methyl-4-csopropylcyclohexadiene-1,3) from 1-methyl-4-isopropylcyclohexa- 
diene-1,3-one-2 by boiling it with alcoholic potash lye. The constants of this preparation 
have already previously been communicated by W. A. Roth and K. von Auwers?): 
b. p. 65.4 to 66° (13.5 mm.); d=2° 0.8353; npisco 1.47942. This synthetic terpinene was 
oxidized by treating it for three hours with ozone in glacial acetic acid. After the 
ozonides had been decomposed, the mixture was first driven over in vacuo and then 
treated with steam. The oil obtained from the distillate proved to be identical with” 
- a, a-dimethylacetonylacetone (semicarbazone, m.p. 200°). The oxidation into this ketone 
proves that the hydrocarbon is identical with e-terpinene,; or at least contains this 
substance as essential component. The constant b. p. indicates that it is present in a 
very pure’ state. 
As to the rotatory power of some derivatives of 6-phellandrene, see page 7. 
Alcohols. 
Allylisoallylearbinol. In a communication on Wagner-Saytzeff’s reaction with open- 
chain aldehydes, C. J. Enklaar*) describes the preparation of allyl¢soallylcarbinol from 
crotonaldehyde. As this reaction may, perhaps, be applied to aldehydes of the terpene — | 
series, we are going to discuss it here briefly. The author gradually, and under cooling, 
added a solution of allyl bromide and crotonaldehyde in an equal volume of ether to | 
zinc wool in a flask with reflux condenser. In order to start the reaction, a little 
heating was required and, finally, it was necessary to heat for some time on a water- 
bath. The mixture was then poured into water, the zinc hydroxide dissolved by adding 
sulphuric acid and the acid liquid treated with ether. The allylisoallylcarbinol, C;H12O, 
boiled between 156 and 156.7° at 765 mm.; d“3- 0.8668; npjs.70 1. 45527. On being heated 
with potassium bisulphate, the alcohol readily splits off water. 
Bupleurol glycol. With the aid of sodium and alcohol, V. Longinow*) reduced the 
ethyl 6-methylheptane-1,3,3-tricarboxylate to the glycol 7-methyl-3-hydroxymethyl- 
octane-1-ol (8-7s shexyltetramethylene glycol), CHs:CH-CHe-CH,-CH:-CH- CH: - CH: OF. 
CH, CH, OH 
This glycol may be looked upon as a derivative of bupleurol®), for which reason 
Longinow calls it bupleurol glycol, in analogy with citronellol glycol. It is a colourless 
liquid boiling at 160° (9 mm.); dae 0.9277; npx0 1.4555. The diacetyl compound boils 
between 151 and 152° (9 mm.); d2> 0.9660; npx»0 1.4369. On being heated with sulphuric — Bs 
acid of 60 per cent. in excess, the glycol is transformed into the corresponding oxide; 
Le 
1) Berl. Berichte 48 (1915), 1357. — *) Liebigs Annalen 47 (1915), 157. As to the preparation of a@-terpinene 
from o-cresol, see K. von Auwers and F. von der Heyden, Berl. Berichte 42 (1909), 2420; Report October 1909, 
172. — *) Berl. Berichte 49 (1916), 211. — *) Journ. russ. phys. chem. Ges. 47 (1915), 1132; Journ. chem. Soe. 
108 (1915), I. 935. — Chem. Zentralbl. 1916, 1. 1054. —~ 5) See Report October 1913, 28. 
ae © the methyl « ng ar the + anltjeiride vields a Uepeatcarbazoie melting between 173 and ~ 
peat 1740, a phenylhydrazone melting at 135° and a p-nitrophenylhydrazone melting at 173°. 
