IOWA ACADEMY OF SCIENCES. llo^ 



PAROXYMETAMETHYLACETOPHENONE AND SOME. 

 OF ITS DERIVATIVES. 



BY J. G. GOODWIN. 



Work leading toward the preparation of this and if pos- 

 sible toward one of its isomers, was commenced with work 

 on phenol. First the phenyl acetate was made as follows: 

 forty-one grams of phenol were taken in a distilling flask, 

 and to this were added gradually, through a reflax conden- 

 ser (in hood) twenty-eight to thirty grams (excess) of acetyl 

 chloride. The flask was heated in a water-bath until the 

 HCl ceased to come off. The contents of the flask were 

 then washed with a dilute solution of sodium hydroxide, 

 brought into a separating funnel with water, and the oil 

 separated, dried over calcium chloride and distilled. B. p. 

 = 195'-^. Yield forty grams. The phenyl acetate then 

 made was converted into p. acetjlphenol as follows* 

 forty grams of the acetate were treated with twenty-eight 

 grams of acetyl chloride and fifty grams of dry, powdered 

 aluminum chloride added, with reflux condenser. Ligroin 

 was added for a solvent, and the whole heated on a water- 

 bath for one hour. The contents of the flask were poured 

 into water, and the oil dried and distilled in fractions as 

 high as 200*^. The part below 132'-' was counted ligroin. 

 The part undistilled was small and caused bumping on 

 further heating. The fraction 132^^ — 200'-' was treated with 

 strong sodium hydroxide in a flask to hydralize it, the un- 

 hydrallized portion being kept for subsequent treatment. 

 The alkaline liquid was acidulated with dilute sulphuric 

 acid, and the oil separating out extracted twice with 

 ether. The portion above 200^ was treated in a similar 



