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5 REPORT OF SCHIMMEL & Co. OCTOBER 1914) APRIL 1 1015. > 
have here to deal with the same bodies. The 2-phenyl-p-cymene meneame aireare ¥ 
by Klages, was obtained by boiling phenylmenthatriene with sulphuric and glacial — 
acetic acids. The action of magnesium benzyl chloride on carvone produces three 
bodies, the principal one being a ketone, 6-benzyl-»-menthen-8 (9) -one-2 (6-benzyldihydro- 
‘carvone); m.p. 73°; b.p. 181 to 184° (11 mm.); oxime, m. p. 140 to 141°. This ketone 
did not yield any semicarbazone with semicarbazide, but an addition product, CisH27N2Oo. 
Besides, there forms from magnesium benzyl chloride and carvone a hydrocarbon, 
CizHoo, (b. p. 162 to 166° at 10 mm.), and another of the same empirical composition, - 
but which boils between 169 and 173° (10 mm.). When the mixture of these hydro- 
carbons was treated with sulphuric and glacial acetic acids, 2-benzyl-p-cymene resulted 
(b. p. 165 to 167° at 12 mm.). e-methylbenzyl magnesium bromide reacts with carvone 
under the formation of an optically inactive hydrocarbon, CisHo0, melting at 127°. 
Through the action of Grignard’s salts on benzyldihydrocarvone, secondary alcohols 
are obtained, from which potassium pyrosulphate splits off water with formation of 
hydrocarbons. In this way magnesium methyl iodide and 6-benzyl-p-menthen-8 (9)-on-2 
afforded 6-benzyl-2-methyl-p-menthen-8 (9)-ol-2, boiling at 188 to 190° (10 mm.), from 
which 6-benzyl-2-methyl-p-menthadiene-2,8(9) (b. p. 169 to 172° at 11 mm.) was prepared 
by dehydration. The authors further describe the corresponding propyl, phenyl and 
benzyl compounds. 
By treating benzyldihydrocarvone with phosphorus pentachloride and reducing the 
chloride formed with sodium and alcohol, one arrives at a diolefinic hydrocarbon 
Ci;He2, presumably 6-benzyl-p-menthadiene-2,8(9) (b. p. 167 to 169° at 14 mm.). The 
action of ozone on benzyldihydrocarvone (6-benzyl-p-menthen-8(9)-on-2) produces an 
ozonide, which has not been investigated more closely so far, but which easily passes 
into a diketone melting at 78°, 1-methyl-6-benzyl-4-acetylcyclohexanone-2; dioxime, 
m.p. 195 to 196°. The same diketone forms, although less readily, when benzyldihydro- 
carvone is treated with chromic acid or potassium permanganate. When melting 
6-benzyl-p-menthen-8(9)-on-2 with caustic potash, carvacrol was obtained. 
A. Claus and W. Fahrion, as well as Schimmel & Co.*) indicate 210 to 211° as 
melting point for the combination of carvone with hydrogen sulphide, whereas according © 
to A. Beyer”) (Copenhagen) it melts at 187°. Of late, E. Deussen*) occupied himself 
whit this combination and found that d- and /-carvone hydrogen sulphide really melt 
at 210 to 211°. The determination of the freezing points showed that the combinations 
behave like dimolecular bodies in benzene, but like monomolecular ones in glacial — 
acetic acid. For a solution of about 6 p.c. in chloroform, the following values of | 
specific rotation were found: [@]piso + 48,719 and [@]p220—48,44°. Inactive carvone 
hydrogen sulphide, however, melts at 189 to 190°. In order to purify the substance, 
it was precipitated from chloroform by means of ethyl acetate. 
Deussen further describes some experiments to brominate carvoxime and benzoyl- 
carvoxime. He added 3 atoms of bromine to d- and /-carvoxime dissolved in chloroform, 
cooling very strongly, and obtained a tribromide: m. p. 119 to 128°; [@]pi0 —15,17° 
and + 14,87° in an about 6,7 p.c. solution in benzene. The inactive compound melted — 
at 128°. In the same manner he prepared the tetrabromide of d- and J/-carvoxime. 
The direction of the rotations ([@]px20— 10,70° and [«]p250-+11,09° in an about 8 p.c. 
solution in benzene) was opposed to that of the raw material. The inactive compound — 
1) Journ. f. prakt. Chem. Il. 89 (1889), 365; Report April 1898, 47, foot note. ay 2) Arch. der Pharm. “ig 
221 (1883), 285. — %) Journ. f. prakt. Chem. Il. 90 (1914), 318. a 
