( 20) 



Chemistry. — ''The formation of salicylic acid from sodiwn 

 phenolate.'" By Dr. J. Moll van Charantk. (Coinmimicated 

 by Prof. A. P. N. Franchimont). 



(Communicated in the meeting of April 27, 1906). 



The communication from Lobry de Bruyn and Tijmstra read at 

 the meeting of 28 May 1904 and tlieir subsequent article in the 

 Recueil 23 385 induced me to make this research. Their theory, 

 and particuhirly the proofs fuiven in support do not satisfy me and 

 as, in consequence of other work, I had formed an idea of the 

 reaction I made some experiments in that direction. 



According to my idea, an additive product of sodium phenokite 



yv'iih. sodium phenylcarbonate, or what amounts to the same an 



additive product of two mols of sodium phenolate with one mol. of 



carbondioxide C6H50C(ONa).^OC6H5 might be the substance which 



undergoes the intramolecular transformation to the salicylic acid 



OH derivative and then forms, dependent on the tem- 



y perature, sodium salicylate and sodium phenolate 



\ j; or else phenol and basic sodium salicylate. This 



\<C.^ view is supported by previous observations of 



V. various chemists and has been partially accepted 



0C« H, ^^Iso by Claisen '). 



As Lobry de Bruyn and Tijmstra give no analytical figures in 

 their paper it did not seem to me impossible that the phenolsodium- 

 ö-carboxylic acid obtained by them might be the substance formed 

 by intramolecular transformation of my supposed additive product. 

 I, therefore, took up their method of working, OH 



prepared sodium phenylcarbonate in the usual /^ 



manner, from sodium phenolate and carbon dioxide, ^«"^4 UJNa 

 and heated this to 100° in a sealed tube for 100 t(r\y,i 



hours. On opening the tube considerable pressure was \ 



observed. This pressure was always found when QQ H 



the experiments were repeated. The gas liberated proved to consist 

 entirely of carbondioxide and amounted to 74 — Va of that present 

 in the sodium phenylcarbonate. H' we argue that the sodium phenyl- 

 carbonate under these circumstances is [)artia!l3' resolved into carbon 

 dioxide and sodium phenolate the latter compound ought to be present 

 or else the splitting up might give carbon dioxide and my supposed 



1) B. B. (1905) 38 p. 714. 



