116 IOWA ACADEMY OF SCIENCES. 



equivalents of the cresol and acetyl chloride, or a slight 

 excess of the latter, and add anhydrous sublimed ferric 

 chloride in c(uantities equal to the chloride. After the 

 action the dark, syrup-like li((uid is poured into water and 

 the insoluble residue distilled with steam. The ketone 

 passes over as an oil and solidifies. It is recrystallized 

 from dilute alcohol. The solvent used in the first of these 

 operations is carbon disulphide. The product out of o. 

 cresol is colored brown by ferric chloride. We shall speak 

 of this test again. 



Nearly all these methods were tried in the laboratory. 

 The method of Verly with large quantities of the phenol, 

 aluminum chloride, low temperature and vacuum did not 

 give a good yield of anything except the ester instead of 

 the oxyketone. This was tried with phenyl benzoate and 

 benzoyl chloride. The method was also tried with acetyl 

 chloride and phenyl acetate, but the esters remained 

 practically unchanged. 



I next I tried p. acetyl phenyl acetate, from phenyl 

 acetate and acetyl chloride by means of zinc chloride and 

 heat to 100° in oil bath. The temperature was kept at 

 100"^ as long as HCl was evolved. The yield was very 

 small. 



The phenyl acetate for these latter reactions was made* 

 as follows: To 60 g. of phenol 80 g. of powdered anhydrous 

 sodium acetate was added in a flask and shaken, then 85 g: 

 of acetic anhydride added gradually through a reflux air- 

 condenser. The temperature of the oil bath was gradually 

 raised to 150 and kept up until the liquid ceased to appear 

 in the condenser. After cooling, water was added and the 

 oil washed in a separating funnel, dried over calcium 

 chloride and distilled at 195 ; tlie yield was 69 g., or 63 

 per cent of the theory. 



Repeated trials of zinc chloiide and aluminum chloride 

 failed to give any satisfactory product. Resort was then 

 had to anhydrous ferric chloride. 5 g. of phenol dissolved' 

 in 5 g. carbon disulphide were taken in a small flask and. 

 6 g. of acetyl chloride added. To them, by means of a rubber 



