PRY ty SP Oe 
146 REPORT OF SCHIMMEL & Co. APRIL 1914. 
Without entering into experimental details, we may here refer to a paper by i 
J. Houben and E. Willfroth') on camphene carboxylic amides and hydrocamphene 
carboxylic amide’). Chloro-allo-camphane carboxylic amide, when simply boiled with 
water, loses all its chlorine in the form of hydrogen chloride and is converted into 
an unsaturated amide: camphene carboxylic amide. Fuming hydrochloric acid re-con- 
verts the amide into the original substance. Reduction by means of platinum and 
hydrogen by Fokin-Willstatter’s method causes the camphene carboxylic amide to 
become hydrogenated into a saturated compound which differs altogether from allo- 
camphane carboxylic amide and may possibly be identical with hydrocamphene 
carboxylic amide. Houben and Willfroth converted the acid mixture which had been 
obtained from chloro-allo-camphane carboxylic ester by treatment with methylalcoholic 
potash into the acid chlorides (using thionyl chloride) and treated these acid chlorides 
with ammonia. By this method they obtained various amides, including two isomeric 
unsaturated amides, of which one (m. p. 209°) proved to be identical with camphene 
carboxylic amide. In conclusion the authors attempted to saponify the amide which 
they had obtained by the hydrogenation of camphene carboxylic amide into hydro- 
camphene carboxylic acid, but this experiment resulted in an acid, m.p. 126°, which 
differed from allocamphane carboxylic acid: possibly a hydrocamphene carboxylic acid 
or zsocamphane carboxylic acid. 
Hydroxycamphenilanic acid. The lead salt of hydroxycamphenilanic acid 
(camphenylic acid), when subjected to dry distillation, gives rise to a yellow diketone 
CioHisO2, to which S.V. Hintikka*) gives the name carbocamphenilone. This body 
occurs in lemon-yellow prisms, m.p.58 to 59°. When oxidised with hydrogen peroxide 
it is converted into an acid, m.p.136°; which is most probably identical with camphene 
camphoric acid. 
Cinnamic acid. H. Stobbe and C. Schénburg*) believe that, as the result of a 
thorough investigation into the subject, they have solved the problem of the chemical 
difference®) between allocinnamic acid with m. p. 67° and the two ‘zsocinnamic acids 
melting respectively at 58 and 42°. The solutions of the three acids differ, because 
under stated conditions they are capable of being recrystallised without undergoing — 
change, and because it is possible to prepare unequal solution-mixtures of any two 
of the acids. The 68°- and the 58°-acids undergo chemical changes during melting. 
The constitution of the mixtures is regularly dependent (apart from the nature of the 
melted acid), upon the period and the temperature of the heating of the fluxes. The 
- preparations which result when the solution mixtures are evaporated and when the 
fluxes solidify, melt respectively at 68°, 58° or 42°. The 68°-preparations constitute 
practically pure allocinnamic acid. The 58°- and the 42°-acid preparations do not 
constistitute uniform isocinnamic acids, but crystal-mixtures (solid solutions) of two or 
three acids, in which the acid with the lowest b. p. which is present in excess, always 
acts as the solvent. 
The miscibility (@.e. the solubility) of the solid acids with higher m. p. is restricted. 
It follows therefore that saturated, unsaturated and super-saturated solid solutions must 
exist, and hence that the 58°- and the 42°9-acid preparations may also differ quanti- 
tatively. The 58°- and the 42°-crystal mixtures are capable of being segregated, the 
1) Berl. Berichte 46 (1913), 2530. — 2) Comp. Report October 1913, 150. — 3) Berl. Berichte 47 (1914), 
512. — 4) Liebigs Annalen 402 (1914), 187. — 5) Comp. Report October 1906, 150; April 1907, 155; April 1909, 
138; October 1909, 210; April 1910, 188; October 1910, 203; April 1912, 192. 
