Phenyliodide Chloride and I odosobenzene Acetate. 551 
tween 185° — 190°. Further elevation of temperature caused only 
decomposition and charring to take place. 
( b ) The experiment was repeated using the same quantities 
of material, and after distilling off the alcohol and ether at 
ordinary temperatures the residue was distilled in vacuo, three 
fractions being collected: 
(1) at ordinary temperatures consisting of alcohol and 
ether ; 
(2) at the temperature of boiling water consisting of 
phenyliodide 
and (3) using the naked flame, when charring took place and a 
colourless liquid distilled over and solidified in the 
receiver. 
This was re-distilled in vacuo and gave a solid melting at 76° C. 
Melting point of ethane-tetracarboxylic ester = 76° 0. 
The solid was re-crystallised from ether and again gave the 
melting point 76° C. 
On combustion : 
•2014 gave *3884 CO, and 1262 H„0. C = 52 59 %, 
H = 696%. 
CuH^Og requires C = 52'83 °/ Q . H = 6 - 91 °/ 0 . 
(c) The experiment was repeated using the same quantities 
as before, but the reaction-mixture was heated on the water-bath 
for several hours under a reflux condenser. A better yield of the 
solid was obtained, and this on re-crystallisation from ether gave 
the melting point 76° C. 
(cl) The same quantities were again mixed together and 
heated on the water-bath under a reflux condenser for several 
hours. Steam was then conducted through the mixture, after 
the salt had been filtered off and the alcohol and ether distilled 
from it. 
Phenyliodide came over, and on standing for a while the 
residue in the flask yielded long slender crystalline needles. 
These on re-crystallisation from ether gave the melting point 
76° C. 
(e) Lastly, the reaction was proceeded with in the cold using 
the above quantities, distilled water was added to the mixture, and 
the whole extracted with ether. On allowing the ether to evaporate 
in the air, phenyliodide remained behind, from which long needles 
crystallised out and these on re-cfystallisation from ether gave a 
melting point 76 D C. 
The action of phenyliodide chloride on monosodium malonic 
ester under the conditions employed thus gives the ethyl ester of 
ethane tetracarboxylic acid instead of a compound containing tri- 
valent iodine. 
