On dry distillation of lead None ueuae ae in an auneegneres of “CO; 
is formed; m. p. 93 to 94°; semicarbazone, m. p. 196.5 to 197. Bris ; 
comparatively readily soluble in water and turns oily when in contact 
a very volatile body of intense, biting smell and Dune iste In. case ie 
and in case it could be made easier ecesoe le “the authors are of opinion | 
body may become important for therapeutic purposes’). Brg tr 
On the phytochemical reduction of methylheptenone, viele p. ay of this Se ee 
: le. nel a eyee 
Eucarvone.— As is generally known, ‘eucarvoxime, on reduction with pa ac 
and hydrogen, yields #-dihydroeucarvoxime, m. p. 123°, and the latter, on hydr 
&-dihydroeucarvone (I)*). The ketone, in glacial acetic acid solution, adds — teadily 
bromine with formation of a dibromide, m.p. 71 to 72°, to which the. formula of as 
1: 7-dibromo-1 : 4: 4-trimethylcycloheptanone-2 (II) is assigned, and on which Wallach a 
brings new details. The body is isomeric with the bromide (III) (m. p. 68°), resulting — 
on direct bromination of tetrahydroeucarvone. The bromide of the m-p. 71 to 72° 
reacts readily with caustic potash, yielding volatile products and an acid. Amongst _ 
the former, a halogen-free ketone predominates which resembles none of the ketones _ 
of the eucarvone series. Evidently, a far-reaching transposition has taken place. The © 
ketone yields very readily a semicarbazone, m.p. 194 to 195°, from which either. an 
open-chain formula, or a side-chain position of the carbonyl group may be inferred. 
With palladium and hydrogen it is converted into a saturated ketone; semicarbazone, 
m. p. 196 to 197°. The alkaline liquid contained an acid CioHieOs,. m. p. 104 to 10: 
which on careful oxidising with permanganate passed over into an acid, m. p. 201 
202°. Evidently the acid CioHisQ2 is identical with a-cyclogeranic acid (IV). (isogerat 
acid) obtained by Tiemann and Semmler from citral. For reason of a direct comparis 
Wallach prepared the latter acid which is easily accessible by abstracting 1 water fr 
citral oxime by means of acetic anhydride, by Sag ae the resue nitrile ae 
no depression of the m.p. when mixed with the acid from dihydroeucarvane aipigie 
of the same m.p. At the same time Wallach established the fact that acyclogera 
acid may be reduced to 1:3: 3-trimethylcyclohexane-2-carboxylic acid by means 
palladium and hydrogen; m.p. 82 to 83°. The formation of e- cyclogeranic acid fre 
the dibromide (Il) is easily explained when Wallach’s formula for 6-dihydroeu 
is see In this case, a super of the heptacyclic ring between the ca 
jections; Therap. Monnians 30: (1916), 342. In the patent apecitication, the reaal solubility i 
water is emphasised. — 7?) Wallach, Liebig's rile. 408 M1714), 1; eer, fey ao Bro 
Liebig’s Annalen 418 (1919), 53 : ; 
