| a a 
i | tT ” AF te . Ng . an ar Lng; Rect 
% esses " Ate a Ses ; 
‘ * * seat ee " Boh a igi ae 5 aS. wie , 
~C s to ae kowa ry the ideas aE 
ined b wa on reducin, 1e, is in reality a diketone, — ? 
ero rich. they tablished two formulas. It is a heavy, colourless oil, which 
ne turns dark. B. p. 126.5 to 127° (11 mm.); d*> 1.0028. It yields 2 disemicar- 
mecompesys. at 200°, and a dioxime, m. p. 123, to 124°. : 
oo ~ Carvone. When oe to condense acetone -with carvone through heating with — 
hydrochloric acid in a sealed tube, A. Miller) observed the formation of carvacrol. 2 
This phenols was identified by its physical properties and the reaction with eee 
chloride. The isomerization of carvone to carvacrol had been observed already under a 
16 influence of several reagents, but not with hydrochloric acid. / a 
-Miiller further studied the isomerizations of carvomenthol, described by Kondakow 
as and Lutschinin*). He prepared 8-chloro-A°-terpene-2-one according to Goldschmidt and — 
_ Kisser®); it cannot easily be purified, as it is very unstable. It yielded carvacrol on 
~ being heated, which yield may be increased considerably by altering the process. — ay ys 
= 4 
Besides, Miiller has been speculating on some of the intermediate products to. aF 
which these isomerizations give rise, and has been able to confirm Kondakow’s pre- gee 
sumptions in —' respects. — é eta | 28 2 
: / oes =f st 
_ Pulegone. E. Sernagiotto*®) has continued fis studies of the feo evans under the — ; 
influence a ay gee examined the action of oxygen and water on pulegone, when 
: : 
< Seeeaatiianate, viz., acetone and @-methyladipic bid Besides, an dneaeieten ketolactdfie™ = 
| GaoFheOs) is foried, m. p. 183.5°; its oxime melts at 116°. On oxidation with chromic — =a 
acid mixture, the ketolactone yielded acetone and - methylglutaric acid. S38 
. = = 
~ Many years ago, Wallach*) described the conversion of dibromopulegone intone 
Ss genic acid under the influence of alkali as one of the most interesting trans- a 
ope _ formations in the group of Bure pee bonne, such as realizes the change of one = 
penne system into another. . : 2 aaa ae 
a al : 
ae ie eee Le So : 3 — 
Bite et 254 | SCH, a ee nen ae 
| | 3 COsH 
Dibromopulegone. : - Pulegenic acid. pas 
- 
a 
A fresh systematic and extensive investigation®) has now made it clear for him 
that the course of the interaction of dibrominated cyclohexanones and alkali depends — 
ie _ considerably on the position of the bromine atoms in the molecule and that, similar — 
: to. what takes place when pulegenic acid is formed, almost any hexacyclic ketones 
saeoay be converted into pentacyclic ketones, if one only starts from dibromoketones 
2 vith adequate position of the bromine atoms and which it is an easy task to prepare. 
OF two. molecules of bromine are added to cyclohexanone in glacial acetic acid, it — 
seems ed the bromine atoms distribute themselves in juxtaposition to a carbonyl 
Se “ 
we 
5) orn. TUSs. hide. chem. Ges. 47 (1915), 1611; Chem. Zentralbl. 1916, II. 255. — 7%) See Report April 
i ’) Journ. f. prakt. Chem. Il. 93 (1916), 10. — 4) Ibidem Il. 60 (1899), 257. — 5) Berl. Berichte 
Be as . — 8) Atti R. Accad. dei Lincei, Roma (5), 24 (1915), 1065; Chem. Zentralbl. 1916, I. 1147. — pak 
tae ae See Report October 1915, 81. — 4%) Liebigs Annalen 289 (1896), 350; Report April 1896, 44. — °) Nachr. 
__ K, Ges. Wiss. Gottingen 1915, session on July 17¢” ae 
