1908-9.] Life and Chemical Work of Archibald S. Couper. 221 
A succeeding paper by Gerhardfc * introduces us to the problem as it 
presented itself to chemists at that time, eleven years before the founda- 
tion of Kekule’s benzene theory. Gerhardt found two anomalies in the 
behaviour of the ethers of salicylic acid. First, that they give well-defined 
salts when treated with bases. Second, that treatment with chlorine or 
bromine does not lead to substitution in the alcohol radicals, but to the 
formation of ethers of chloro- or bromo-salicylic acid. 
At first Gerhardt gave “ salicylate de methyle (huile de gaultlieria) ” a 
formula similar to that of silver salicylate : — 
C 7 H 5 0 2 ) C 7 H 5 0 2 ) 
V o o. 
OH 3 I Ag ) 
The first of the two anomalies — the only one that interests us here — led 
Gerhardt to regard the ethers of salicylic acid not “ coniine une molecule 
d’eau dont 2 atonies d’hydrogene etaient remplaces l’un par du salicyle et 
l’autre par du methyle ou d’ethyle,” but “ comme une molecule d’eau dont 
1 atome d’hydrogene seulement etait remplace par le groupe methylsalicyle 
ou ethylsalicyle, c’est-a-dire par du salicyle contenant deja lui-meme du 
methyle ou de l’ethyle en substitution a de 1’hydrogene : — 
C 7 H 4 (CH 3 )0 2 j 
O Hydrate de methylsalicyle. 
H ) 
C 7 H 4 (C 2 H 5 )0 2 j 
H 
Correspondingly, he gives the potash salt of gaultlieria oil the formula and 
0 Hydrate d’ethylsalicyle.” 
name 
“ C 7 H 4 (CH 3 )0 2 
K 
0 Oxyde de potasse et methylsalicyle.” 
He adds: — “ L’experience a pleinement justifie mes presomptions. Rien 
n’est plus facile, en effet, que d’etherifier les ethers salicyliques, comme 
on etherifie l’alcool ou l’esprit-de-bois.” For, by treatment with benzoyl 
chloride, the salicylic ethers give the corresponding benzoyl derivatives. 
“ C 7 H 4 (CH 3 )0 2 j 
C 7 H 5 0 ) 
C 7 H 4 (C 2 H 5 )0 2 ) 
0 
C 7 H 3 0 ) 
In order to obtain the “chlorure de methylsalicyle,” Gerhardt sub- 
* Comptes rendus , xxxviii. 32-34, seance du lundi, 9 Jan. 1854. 
0 
Benzoate de methylsalicyle, 
ou oxyde de benzoile et de 
methylsalicyle. 
Benzoate d’ethylsalicyle ou 
oxyde de benzoile et d’ethyl- 
salicyle.” 
