552 
Mr Hodgson, Some Reactions of 
Action of phenyliodide chloride on disodium malonic ester. 
Disodium malonic ester was prepared by adding to T673 grms. 
of sodium wire dissolved in absolute alcohol, 5 ‘8 2 grms. of malonic 
ester. After standing for some time absolute ether was added until 
turbidity just began to appear. 10 grms. of C B H 5 IC1 2 were then 
added in small quantities at a time and the mixture well shaken. 
Heat was developed, and this was moderated by cooling the flask. 
After standing for several days the reaction-mixture was filtered 
and the coloured precipitate formed was found to contain sodium 
chloride mixed with phenyliodide. The alcohol and ether were 
distilled from the solution, and then the whole distilled in vacuo. 
Phenyliodide came over, and then the whole contents of the flask 
charred with decomposition, no further distillate collecting. 
The experiment was repeated, using the same quantities, and 
heating the mixture for several hours on the water-bath under 
a reflux. On filtering the product the precipitate was a pure 
white containing sodium chloride but no sodium and phenyl- 
iodides, thus showing that the reaction takes place much better the 
higher the temperature. On fractional distillation in vacuo only 
phenyliodide came over, excessive charring taking place as before. 
On submitting the precipitates formed in the reaction to 
continued extraction with hot ether and then evaporating off the 
ether from the ethereal solution, crystals were deposited, which, on 
re-crystallisation from pure dry ether gave a melting point 76° C. 
One product of the reaction was therefore the ethyl ester of ethane 
tetracarboxylic acid. 
The same quantities of phenyliodide chloride and disodium 
malonic ester were mixed together as before, and heated for several 
hours on the water-bath under a reflux. After filtering, the alcohol 
and ether were distilled off and the mixture then heated for several 
hours under a reflux with strong KOH. Steam was afterwards 
conducted through the saponified solution, and phenyliodide thus 
got rid of. The residue was then concentrated to a small bulk on 
the water-bath, and glacial acetic acid added until the solution was 
just acid. Rectified spirit was then added to the acid liquid, when 
a greyish white precipitate began to settle down. The mixture 
was allowed to stand for several days and then filtered. The 
precipitate was detached from the filter-paper, and boiled with 
absolute alcohol for a considerable time. Further, the precipitate 
was dissolved in water, and the substance in solution reprecipitated 
by absolute alcohol. After filtering, the solid was dried at 100° C. 
in the air and then in vacuo. The amount of potassium in the 
solid was estimated by converting a weighed amount of the salt into 
sulphate. ’2474 of salt gave '2365 of K 2 S0 4 . K = 42'85 %. 
