IOWA ACADEMY OF SCIENCES. 115 



It may be in order here to speak of some of the different 

 'methods that have been used for forminf? these compounds. 

 We find, for example, that o. oxyacetophenone was made by 

 Y. Tahara from methyl salicylate through o. methoxy- 

 benzoylaceticester and o. methoxyacetophenone.* The last 

 step, that of splitting off the methyl group, was accom- 

 plished by digesting for six hours the o. methoxyacetophe 

 none with concentrated HCl at 150 in a sealed tube. 

 Methyl chloride was evolved and also a brown oil which 

 was extracted from its ethereal solution by means of sodium 

 hydroxide and subsequent acidification, extracting with 

 ether and evaporating, when the o. oxyacetophenone 

 appeared in the form of a brown oil which was purified by 

 distillation and crystallization. The sodium salt of this 

 •compound has the form of colorless leaves. The yield is 

 ;small. The acetyl derivative was made by the action 

 of acetyl chloride upon the sodium salt. 



P. Freidlander and J.Neudorfer prepared the o. oxyaceto- 

 phenone from o. nitrophenylpropiolic acid, con verting this 

 into nitro-phenyl acetylene, amidophenyl acetylene, and 

 finally amidoacetophenone. This last named is diazotized to 

 o. oxyacetophenone. The yield is better than that of Tahara. 

 For the acetyl compound these experimenters heated 

 the oxyacetophenone witli acetic anhydride and sodium 

 acetate to 150'. The acetyl compound crystallized out of 

 alcohol in hexagonical plates. M. p. 89^. 



Nencki and Stoeber studied the action of acetyl chloride 

 on bezene and mono-basic phenols in the presence of 

 ferric chloride. f Acetophenone was prepared. Yield 

 not stated. P. oxyacetophenone was prepared from 

 acetyl chloride and phenol, melting point 108^. 150 g. of 

 phenol gave 30 g. of ketone. These men found also that 

 the isomeric cresols acted like the phenols. From o. cresol, 

 p. oxym. methylacetophenone was prepared, m.p. 104 '. Also 

 p. oxy o. methylacetophenone from m. cresol, m. p. 126". 

 Benzoyl chloride yielded no oxybenzoylphenone but only 

 •cresol beuzoate. The method was to take molecular 



♦Berichte 25, pp. 1306-1310. 

 fBeriehte, 3,', p. 1768. 



