cs 18 ; 
~ when the formation of the following yar oGateOnes was ‘observed: ‘dis 
toluene, m-xylene, and 1-methyl-3, 5-diisopropylbenzene, a body unknowr | 
Schorger characterized all of these al | by suitable derivatives. 
Alcohols. 
Cyclohexyl-4-butanol-3. — When cyclohexanol, sec. butylalcohol _and dehydra 
potassium hydroxide are heated for 24 hrs. in a sealed tube to 210 to 220°, there 
results, as has been found by M. Guerbet’), the secondary alcohol cyclohexyl-4-butanol. i 
a colourless liquid of weak but pleasant smell; b.p. 126 to 1279 (31 mm.), digo 0.9 F 
acetate, b.p. 131 to 132° (31 mm.); phenylurethane, m.p. 76°. Oxidation of the alcohol 
by means of potassian bichromate and sulphuric acid led to the corresponding ketone | 
cyclobutyl-4-butanone-3, a pleasant-smelling liquid; b.p. 220 to 222 (758 mm.), doo 0.917. 
The ketone does not react with sodium hydrogen sulphite. Its semicarbazone melts 
at 145 to 146°.. Further oxidation of the ketone by means of potassium bichromate” 
and sulphuric acid yielded a mixture of acetic and cyclohexylacetic acids. | 
C,Hi:-OH + CH3-CHOH:CHe:-CH; = CeHi1-CH2: CHOH: CH: CH; -- HO 
Cyclohexanol. sec. Butylalcohol. Gyetohexyl: -4-butanol-3. a 
Se 
a 
Menthol. —The menthyl chloride originating from the action of phosphorus penta- 
chloride or concentrated hydrochloric acid on menthol is no uniform substance, bal 
a mixture of at least two isomerides. Pure methyl chloride proper was prepared | at 
one time by M. J. Kursanov2) by boiling the crude product with alcoholic potash o : 
aniline. Recently, the same author®), in order to study the composition of raw menthyl 
chloride, has investigated the different menthane. carboxylic acids resulting therefrom. i 
The stable menthyl chloride yields only one menthane carboxylic acid, m.p. 65 to 669, 
the raw product yielding also a liquid acid. No stereoisomeric transformation takes i 
place where phosphorus trichloride acts on the solid acid, since the chloro-anhydride _ 
obtained can be retransformed into the original acid. The acid of the m.p. 65 to 66° 
([“]p —54.23° in benzene solution) yields a crystalline amide, m.p. 151°; the liquid 3 
acid is possibly a mixture of several isomeric acids. ea 
In order to investigate the composition of “menthyl chloride’, Kursanov4) studiedl 
the behaviour of two different preparations obtained by the action of phosphorus penta= 
chloride on a solution of menthol in light petroleum. The one boiled from 90 to 959 
(16 mm.) (#) — 10.68° [in a 20 cm. tube]), the other from 91 to 96° (16 mm.) (ep — 14. oe 
[in a 20 cm. tube]). Both preparations were repeatedly heated with alcoholic potash ae 
and each time the volatile portion removed and undecomposed chloride again heate d 
with alcoholic potash. It was found that the optical rotation of the first fracti 
increased at first, then decreased; in the ead, the positive rotation ‘changed into 
negative. ; 
Since the stable menthyl chloride, even after mixing it with menthyl cn 
alcoholic potash, Kursanov assumes that the crude Be is compc s 
_mixture of the stable menthyl chloride, two secondary chlorides of different 
1) Bull. Soc. chim. IV. 28 (1918), 78. — %) Comp. Report October 1901, 72. — *) Jc “rn. 
chem. Soc. 48 (1916), 862; Journ. chem. Soc. 112 (1917), I. 137. — 4) Journ. Russ. phys.-chem. 
367; Journ. chem. Soc. 112 Saige . 151. 2 Sha SIN at Se a 
