TITE GEIGNARD REAGENT ON 0-PRTHALIC ESTERS, 7 



facts and that l:l-diphenyl-3-phenylene-phtbalane to be presently 

 described contains the double ring <f^- 



Experimental Part. 



I. The action of methyl magnesium iodide on o-phthalic 

 acid diethyl ester. 



An ethereal solutioa of the Grigiiard reagent was, according 

 to the ordinary method, prepared in a large round bottomed 

 flask (capacity 1.5 litre), having a pretty wide side tube, through 

 wdiich the foot of a dropping funnel passed and was fixed by means 

 of a good cork, and the mouth of the flask was connected w^ith 

 a long reflux condenser, both the dropping funnel and the con- 

 denser being, in turn, connected with a U-tube filled with soda- 

 lime and calcium chloride, in order to keep away moisture and 

 carbon dioxide. 



When all the methyl iodide had been added through the 

 dropping funnel and nearly the whole of the magnesium powder 

 dissolved, phthalic acid diethyl ester, diluted with four times its 

 volume of absolute ether, was introduced through the dropping 

 funnel in the proportion of one molecule of the ester to four of 

 the Grignard reagent, the whole being well cooled with ice and 

 water. A clearly visible reaction took place, and, as it ap- 

 proached towards the end the contents of the flask were found 

 to be separated into two layers, which, after standing for about 

 twenty hours, were decomposed by adding ice and dilute sulphuric 

 acid. The ethereal layer, w4iich now separated from the aqueous 

 solution, was drawn oft" and well washed, first, with a dilute 

 solution of sodium carbonate and, then, seveval times with pure 

 water. On distilling off* the ether, there remained a very thick 



