(21) 



intermediary product (CgHsO')^ C(0Na)2. In the first ease it is strange 

 that during the cooling of the tube, which often was left for a few 

 days, the carbon dioxide is not greatly reabsorbed. Those substances 

 had now to be searched for in the product of the reaction. On 

 treatment with ether a fair amount of phenol was extracted although 

 moisture was as much as possible excluded. It was then brought 

 into contact with cold, dry acetone, by which it was partially dissolved, 

 but with evolution of gas and elevation of temperature. From the 

 clear solution, petroleum ether precipitated a substance which, after 

 having been redissolved 'and reprecipitated a few times in the same 

 manner, formed small white needles containing acetone which efflo- 

 resced on exposure to the air. On analysis, this compound proved 

 to be sodium salicylate with one mol. of acetone. As an ebullioscopic 

 determination in acetone, according to Landsberger, did not give the 

 expected molecular weight, sodium salicylate was dissolved in acetone 

 and precipitated with petroleum ether and a quite identical product 

 was obtained as proved both by analysis and determination of the 

 molecular weight. Both products, after being dried at 100°, yielded 

 no appreciable amount of salicylic ester when heated with methyl 

 iodide. 



The amount of sodium salicylate obtained by heating sodium 

 phenylcarbonate in the manner indicated was, however, very trilling. 



I suspected that the evolution of gas noticed in the treatment with 

 acetone, and which was identified as pure carbondioxide without 

 any admixture, was caused by the presence of unchanged sodium 

 phenylcarbonate, so that, therefore, the reaction was not completed, 

 and that the tube after being heated must still contain a mixture of 

 unchanged sodium phenylcarbonate, sodium phenolate, sodium sali- 

 cylate and free phenol, besides the said additive product (CbHbO)^ 



OH 



C(0Na)2 and the salicylic acid derivative possibly CgH^ ONa 



formed from this. I now thought it of great \y 



importance to first study the behaviour of acetone CONa 



with these substances as far as they are known. /-^n u 



(Jug Hj 



Sodium phenolate dissolves in boiling acetone, from which it 

 crystallises on cooling in soft, almost white needles, several cm. Ion"-, 

 which contain one mol. of acetone. They lose this acetone, in vacuo, 

 over suli)huric acid. At the ordinary temperature acetone dissolves 

 only 0,1 7„. 



Sodium phenylcarhonate placed in cai-efuUy dried acetone gives otf 



