114 IOWA ACADEMY OF SCIENCES. 



manner. When the hydrolysis would })roceed no further, 

 the ether was distilled off over a waterbath, and set aside 

 for evaporation. The portion from the 132^ — 200^ fraction 

 crystallized in long needles, that of higher boiling point 

 remained an oil even at -17*^. The crystals melted at 107^ 

 and were soluble in warm water and in the usual organic 

 solvents. 



The product is p. acetylphenol. This shows that the 

 first acetyl group going on was split off and the hydroxyl 

 restored by hydrolysis, the acetyl group para to it remain- 

 ing. In putting on the second group the halogen acid was 

 split off from the acetyl group. This cleavage was next 

 tried with anhydrous zinc chloride as an agent, instead of 

 aluminum chloride. This is said^ to be of advantage, 

 especially where organic radicals are to be introduced into 

 the nucleus of phenol, amines, and acids. It is specially 

 used, therefore, for making ketone acids, oxy-ketones, etc., 

 whereby naturally the acid group reacts also with the 

 amido or hydroxyl group, unless, as is better, this has been 

 done first. The ordinary rules for position hold. 



To apply this method three grams of phenol are taken in 

 a large test-tube and to it 4.5 grams of benzoyl chloride 

 added slowly, the whole heated in a water-bath to drive of 

 excess of HCl. Again the same quantity of benzoyl chlo- 

 ride is added and a small quantity of freshly prepared 

 anhydrous zinc chloride added until no further action is 

 caused by it. While this is being added the tube is kept 

 at 180^ by means of an oil-bath. Crystals appear. The 

 mass is brought into alcohol, heated to dissolve, filtered, 

 cooled slowly, when crystals form and are freed from the 

 ' mother liquor by means of a filter pump. They are washed 

 with a small quantity of cold alcohol and warmed to drive 

 of the alcohol. The crystals are in the form of leaves and 

 are pressed on a porous plate to dry, and the melting point 

 found to be IIP. The product is p. oxybenzophenonben- 

 zoate. 



Yield 2.2 grams. 



•Elbs. Vol. II, p. 177. 



