IOWA ACADEMY OF SCIEXCES. 117 



tube to exclude moisture, anhydrous ferric chloride was 

 slowly added — -7 g. The flask was kept cool with a water- 

 bath. Tiie contents were poured out into water, the oil 

 distilled with steam to drive off the carbon disulphide and 

 ])henol, the residue filtered hot. Yield 1.3 g. of p. 

 oxyacetophenone. This method was then tried with p. 

 cresol but even after repeated trials refused absolutely to 

 work. Out of o. cresol, j). oxy m. methylacetophenone 

 was prepared. Carbon disulphide was used for a solveiit, 

 with ferric chloride. The yield was 14.8 per cent, of the 

 theory. The flask was kept cool to avoid loss of the solvent. 

 The product was poured out on snow, so that the heat of 

 reaction would not decompose it, and the oil distilled with 

 steam, and purified as above, by crystallization. M. p. 

 104^ 



It appears from the foregoing paragraphs that the place 

 para to the hydroxyl group must be free in order that the 

 cleavage and condensation may take place. Then the fact 

 is, that the acetyl chloride acts on the para hydrogen, even 

 when the hydroxyl group has not been changed or replaced, 

 giving the oxyketone without any hydrolysis. 



It appeared that the yield might be larger if the 

 temperature w^ere higher than that which the German ex- 

 perimenters had used — the boiling point of carbon disul- 

 phide. A higher temperature then was made possible by 

 means of carbon tetrachloride as a solvent, which was used 

 at 65^. The first trial gave a yield of 25 per cent, and this 

 was subsequently raised to 28 per cent, while the best 

 method that had been used by these Germans, Nencki and 

 Stoeber, who used carbon disulphide and low temperature, 

 gave a yield of 14.8 per cent. Repeated experiments showed 

 that the temperature of G5 gave the largest product. A 

 higher temperature gave more tar; at a lower temperature 

 the reaction did not take place to any practical extent. 



After a considerable quantity of this product, the p. oxy 

 m. methylacetophenone had been prepared, I studied to 

 find whether the product described by these chemists, 

 Nencki and Stoeber, was pure. For this purpose the prod- 



