NOTES ON SCIENTIFIC RESEARCH. 101 
melted at 121,59. The benzoylcarvoximes furnish dibromides melting at 140 to 141° 
([@]p20 +5,66° and [@]p40—5,11° in an about 2 p.c. solution in benzene); the inactive 
compound melts at 121°. 
At an earlier opportunity, A: Hahn‘) prepared ZL- and R-d-tetrabromocarvoxime- 
benzoyl esters. When repeating the experiment, Deussen succeeded in splitting the 
tetrabromo compound into two isomerides, wiz. L-d- or R-l-tetrabromo-¢-benzoy]l- 
carvoxime-a, insoluble in alcohol and melting at 136 to 137°, and a L-d- or R-l-tetra- 
bromo-«-benzoylcarvoxime-b, easily soluble in alcohol and melting at 119 to 120°. The 
inactive form of the a-compound melts at 145°; that of the b-compound, at 127 to 127,5°. 
In an article published at the beginning of 1914, O. Wallach’) described the 
reduction of carvone and carvoxime by means of hydrogen and palladium. He 
obtained, according to the conditions under which the experiments were carried out, 
. carvotanacetoxime or tetrahydrocarvoxime, in addition to carvacrylamine and tetra- 
hydrocarvone. An electrolytical reduction of carvoxime in alkaline solution, undertaken 
by H. Rupe and K. Loffl*), yielded a fair quantity of pure dihydrocarvone, in addition to 
unaltered carvoxime. Presumably carvoxime is first reduced to dihydrocarvoxime, which 
is then saponified. The semicarbazone of the dihydrocarvone thus obtained melted bet- 
ween 189 and 191°. No other reduction product of dihydrocarvone could be traced. 
Hexahydro-w-ionone. N. Ishizaka*) reports on the preparation of hexahydro-y-ionone 
and of some of its derivatives. He reduced geraniol according to Paal’s method with 
palladium and hydrogen in methyl alcoholic solution to tetrahydrogeraniol, boiling at 
212 to 213°. In this manner, the hydroxyl group remains unattacked, whereas on 
hydrogenation with platinum and hydrogen®) a mixture of dimethyloctane and dimethyl- 
octanol results. By means of phosphorus tribromide, tetrahydrogeraniol was converted 
into tetrahydrogeraniol bromide (b. p. 104 to 105° at 14 mm.), which with ethyl sodio- 
acetoacetate affords ethyl tetrahydrogeranylacetoacetate (b. p. 164 to 106° at 10 mm.). 
On prolonged standing with alcoholic potash lye the ester is converted into hexahydro- 
w-ionone. The ketone, recovered from the semicarbazone (m. p. 95 to 96°), boils at 119 
to 120° (10 mm.) and has lost its aromatic character. The oxime of hexahydro-y-ionone 
boils at 159 to 160° (13 mm.). 
Phenols and Phenol-ethers. 
The ether-oxides of carvacrol. Following up former treatises on the preparation of 
mixed ethers of alcohols and phenols”), P. Sabatier and A. Mailhe*) report on the 
catalytic production of ether-oxides of carvacrol. In the presence of thorium oxide, the 
dehydration of carvacrol between 400 and 500° is rather complicated. Carbon monoxide 
and hydrocarbons are evolved and an oily mixture of carvacryl and dicarvacrylene 
oxides forms. If a mixture of carvacrol and methyl alcohol is passed over thorium 
oxide at 420 to 450°, in addition to carvacryl methyl ether, dicarvacryl oxide forms, 
C;H ea | 
cH, Cots: O- CoH a substance consisting of colourless prisms which melts 
at 109 to 110° and is soluble in most of the organic solvents. If the catalysis takes 
1) Comp. Report April 1910, 177. — %) Liebigs Annalen 408 (1914),..73; Report April 1914, 142. — 
*) Berl. Berichte 47 (1914), 2150. — 4) Berl. Berichte 47 (1914), 2453. — 5) Comp. R. Willstatter and E. Mayer, 
ibidem 41 (1908), 1475; Report November 1908, 153. — W. Ipatiew, Berl. Berichte 45 (1912), 3218; Report April 
1913, 134. — 7) Compt. rend. 151 (1910), 359, 492. — 8) Compt. rend. 158 (1914), 608. 
