956 
and Gernzemr; this however, is expensive as it starts with malonic 
acid and yields at most only 20°/,. 
The reaction between Na-malonie ester and chloroform took place 
entirely according to the directions of Conrap and Gurnzeir, but 
with sufficient precautions much larger quantities (say 100 grams) 
can be operated with. The yield of Na-dicarboxylglutaconie ester 
recrystallised from alcohol is bad (40—42°/, of the theoretical) but 
as demonstrated by Covrerre) in a very elaborate research it 
cannot be improved. 
From this Na-compound the ester was liberated with dilute acetic 
acid. The saponification of this dicarboxylglutaconic ester to gluta- 
conic acid has been studied elaborately by Gutazeir and Boram *). 
They found that a saponification of the esters with alkalis gave very 
bad results as a considerable portion decomposed into malonic acid 
and formie acid; on the other hand the saponification with hydro- 
chloric acid proceeded fairly rapidly. This, I have carried out as 
follows: 
Portions of 30 grams of the ester were boiled with thrice the 
volume of hydrochloric acid (10°/, HCl) and half the volume of 
alcohol in a Monracne*) reflux apparatus until the evolution of 
carbon dioxide has ceased, which took about seven hours. 
According to Gurnzerr and Boram the reaction mixture must now 
be evaporated until a separation of crystals takes place at the surface ; 
sometimes this succeeds, but frequently the crystallisation does not 
set in and a viscid syrup is obtained chiefly consisting of $-oxyglu- 
taric acid formed by the action of water on the glutaconie acid. 
The best plan, however, is as follows: 
The liquid is neutralised with sodium hydroxide saturated with 
ether, again acidified with sulphuric acid and then extracted conti- 
nuously with ether. After drying over calcium chloride the ethereal 
solution is mixed with benzene and then left to itself, on evaporation 
of the ether a yield is obtained of 50°/, of the theoretical quantity 
of glutaconie acid which is nearly white and melts above 130°. 
The crude acid was titrated with baryte: 
0.1749 gram required 26.55 ec. Ba(OH), 0.1009 n. M. 130.6 
0.1468 „ 5 2277 „ x 0.1009 ,, M. 130.7 
Theory M. 130.05. 
The purification of the acid took place by recrystallisation from 
1) J. pr. (2) 73. 49 (1906). 
2) J. pr. 54. 372 (1896); 58. 407 (1898). 
8) Chem. Weekbl. 7. 375 (1910). 
