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III. On some of the Products of the Decomposition of Nitrotoluylic Acid. 
By Henry M. Noad, Ph.D., Lecturer on Chemistry at St. George's Hospital. 
Received November 17, — Read December 8, 1853. 
In a paper read before the Chemical Society, and published in the third volume, 
p. 421, of the Transactions of that body, I described the mode of preparation and 
properties of two new organic acids, which, from their general analogy to benzoic 
and nitro-benzoic acids, were considered to be the representatives of those acids in 
the succeeding or Toluyl series, and were named accordingly Toluylic (C ]6 H 8 0 4 ) 
and Nitrotoluylic ^C l6 |^^ j() 4 ^ ac '^ s - 
These two acids, interesting as supplying two members of a well-defined series of 
acids, and as establishing a parallelism between the benzoyl and toluyl groups, were 
formed by the oxidation of Cymol, a hydrocarbon (C 20 H u ) occurring with cuminol , an 
oxyhydrocarbon (Cl 20 H 12 0 2 ) in the oil of cumin ( Oleum cumini ), from which source 
alone they have hitherto been obtained. 
The original object in submitting cymol to the action of fuming nitric acid was 
the formation of the substitution compound ^oj^Q 3 j? from which, by the action of 
reducing agents, it was anticipated that an organic base, analogous to those formed 
from nitrobenzole (aniline)*, from nitrotoluole (toluidine)'f-, and from nitrocumole 
(cumidine)^;, would have been obtained: the unexpected formation however of a 
crystalline acid gave a different turn to the investigation, and the search for cimidine 
(C 20 H 15 N) was for the time laid aside. 
I have at various times since the publication of this first paper returned to the study 
of the action of nitric acid on cymol, and have made many attempts, by employing acids 
of various degrees of strength, by keeping down the temperature by surrounding the 
vessels with freezing mixtures, Sec., to check the action of the acid before it had pro- 
duced its maximum degree of oxidation on the oil ; yet though I have in this way 
obtained several beautifully crystallized intermediate products, and amongst them a 
compound homologous to dinitrobenzole, in which two equivalents of the hydrogen of 
the oil have given place to two of hyponitric acid, viz. C 20 | 9 ^q j> still the principal 
* Zinin, Annal. der Chem. und Pharm. Bd. xliv. p. 283. 
f Muspratt arid Hofmann, Mem. Chem. Soc. vol. ii. p. 373. 
J Nicholson, Chem. Soc. Quart. Journ. vol. i. p. 2. 
G 2 
