IOWA ACADEMY OF SCIENCES. 119 



fifteen grams of the purified ether. This was much better 

 than the results obtained by Hoffmeister, but much less 

 than was claimed by Hirsch. 



The process is long and tedious, and the returns so rela- 

 tively small that it was thought best to give attention to 

 other promising methods. 



THE GLADSTONE-TRIBE METHOD. 



Gladstone and Tribe obtained phenyl ether and two or 

 three other compounds by distilling aluminum phenolate, 

 prepared by acting on phenol with aluminum, in the pres- 

 ence of iodine as a catalytic agent. They estimated that 

 one-half of the aluminum phenolate was decomposed by 

 the action of heat into phenyl ether and aluminum oxide. 

 That being the case, the distillation of aluminum pheno- 

 late would be an excellent method by which to prepare 

 phenyl ether, providing the aluminum phenolate could be 

 easily obtained. 



Preparation of the Aluminum Pltenolate. — Five hundred 

 grams of phenol containing a gram or so of iodine in a 

 flask fitted with a return condenser was heated over a 

 direct flame, and the aluminum, in the form of strips, venj 

 slowly added. It was found necessary to obey this pre- 

 caution very carefully, since, when considerable quantities 

 of aluminum were added at a time, the action was so vio- 

 lent that the heat of reaction raised the phenol to its boil- 

 ing point and volatilized it so rapidly that it projected from 

 the tube uncondeused. 



Properties of Aluminum. Phenolate. — The solid substance 

 is brittle and possesses a vitreous luster and conchoidal 

 fracture. Prepared as given above, it is usually black, but 

 sometimes gray. It is soluble in hot xylene, from which it 

 separates as a gelatinous mass on cooling, and Gladstone 

 and Tribe found it to be soluble in benzene. If bottled 

 tightly it can be kept for a long time without undergoing 

 any change, but if allowed to come in contact with the air 

 it very soon loses its vitreous luster and crystalline grains 

 appear throughout the surface of the fragments. It 



