106 REPORT OF SCHIMMEL § Co. OCTOBER 1914/ APRIL 1915, bia 
other bodies; the condensation of ethylmonomethyl succinate with ethyl oxalate, when 
ethyloxalylmonomethyl succinate results; the preparation of ethyl «,«-dimethylbutane- 
y-one-«, 0, 0-tricarboxylate; the synthesis of ethyl «,«-dimethylbutane-y-ol-a, y, 0, 0-tetra- — 
carboxylate and the corresponding lactone, as well as the production of butane-a, @, 0-tri- 
carboxylic acid. 
Camphenic acid is to be considered, as O. Aschan*) says, a secondary oxidation 
product of camphene and forms owing to a transposition of camphenylic acid. 
By heating with concentrated potash lye he succeeded in immediately converting 
camphenylic acid into camphenic acid. For this purpose, sodium camphenylate, 
obtained as a by-product of the oxidation of camphene with potassium permanganate, 
was cautiously melted in a silver crucible with potassium hydroxide. The thus resulting 
acid melted at 130 to 131° and did not cause any lowering of the melting point, when 
mixed with pure d,/-camphenic acid. 
The lead salt of camphenecamphoric acid affords on distillation the corresponding 
ketone, which is identical with camphenilone’). As Lipp prepared camphenecamphoric 
acid synthetically, it follows that the production of camphenilone from camphenic acid 
represents a complete analysis of camphenilone. In consequence, it is beyond doubt 
that the formula as per margin expresses the con- 
eC CH C(CHs)s stitution of camphenilone. The semicarbazone of 
| CH, camphenilone melts at 224°; camphenilone purified 
| | by way of the semicarbazone, at 36°. 
On dry distillation of the calcium salt of 
Camphenilone (a, a-dimethyInorcamphor). | Camphenecamphoric acid no camphenilone resulted. 
Dehydrocamphenic acid. Simultaneously and independently from each _ other, 
S. V. Hintikka and P. Lipp*) established for the lactonic dibasic acid, CyHi20¢ 
(m. p. 256°), which Aschan*) obtained by oxidizing dehydrocamphenic acid with nitric 
acid, the formula of a lactone of «-hydroxyisocamphoronic acid. This is opposed to 
Aschan’s supposition, who looked upon this body as a lactone of a,a-dimethyl- 
8-hydroxyadipic-s-carboxylic acid. Lipp*) studied the subject further and found that 
isocamphoronic acid, on 
H.C ———- CH——C(CHs). oo geile gM ca heating with bromine in— 
to bo.H | HC-0:CO a sealed tube until the 
Tl ; | bromine colour disappears, 
H.C C-CO.H CO:.H CO.H yields a product of the 
Dehydrocamphenic acid. Lactone of a-hydroxyisocamphoronic acid. composition CoHi2O06, HeO, 
melting at 185 to 186°. 
On further heating, a lactonic carboxylic acid, CyHi2O¢, results (m. p. 253 to 254°). 
These two bodies proved in all their properties to be identical with the lactonic di- 
basic acid derived from dehydrocamphenic acid and its isomerides. Owing to this 
investigation, it may be taken for established that the body CyHi2O., (m. p. 256°) 
from dehydrocamphenic acid really is the translactone of e«-hydroxyisocamphoronic 
acid and that the stereomeric product (m. Ri, 182. to 186,5°) is to be regarded as the 
cis-modification. 
“¢ € 
S 
~1) Berl. Berichte 47 (1914), 1121. — 7) G. Komppa 205, s. V. Hintikka, Berl. Berichte 47 (1914), 1550. —_ “a 
3) Ann. Aced. Scient. Fennicae A. 5 (1914), No. 3. — Berl. Berichte 47 (1914), 872. — 4) baie Annalen 875 
(1910), 369; Report April 1911, 188. — 5) Berl. Berichte 47 (1914), 2994. ; 
