P. A. Levene and L. H. Cretcher 507 
mit the isolation of intermediate products of oxidation of the 
tertiary hydrocarbons. 
EXPERIMENTAL. 
Diethyl Dibutylmalonate. 
COOC.H; 
Cu i 
a 
C.H,” | 
COOC.H; 
This ester was obtained by the action of butyl iodide and sodium 
ethylate upon diethyl malonate. One molecule of sodium ethylate 
and one of butyl iodide were added to malonic ester and the mix- 
ture was boiled until neutral. After the first substitution was 
complete another molecule of sodium ethylate and butyl iodide 
were added and the mixture was again boiled on the water bath 
until it was no longer alkaline to litmus. The attempt to make 
both substitutions at the same time, z.e. by heating the malonic 
ester with two molecules of sodium ethylate and of butyl iodide, 
gave unsatisfactory results. Diethyl dibutylmalonate boils at 
153=154° at 14 mm. (corrected). 
0.1006 gm. substance gave 0.2464 gm. CO, and 0.0938 gm. H.O. 
Calculated for Found: 
15f128U4: 
is? an ae ae ie ea tae OS Oe Ore 66.58 66.80 
fA esos Sit cP AC aE as Mem Ne rae Gehl, ln he 10.29 10.42 
Debutylmalonic Acid. 
This substance was prepared by the saponification of the cor- 
responding ester in the following manner. Malonic ester was 
converted into diethyl dibutylmalonate as described above. For 
the preparation of this acid in quantity the ester was not iso- 
lated, but to the alcoholic solution of the ester resulting from 
the treatment of malonic ester with sodium and butyl iodide 
there was added a solution of potassium hydroxide in the mini- 
mal amount of water. The solution was boiled on the water 
bath under a reflux for 10 hours to complete the saponification, 
the mixture was then transferred to a large beaker, the alcohol 
