Feb. 16, 1914 
Benzene Derivatives in Soils 
359 
On elementary analysis this compound gave the following results (0.200 
gram were used for each analysis): 
Analysis i. Analysis 2. 
Per cent. Per cent. 
Carbon..... 63.33 63.02 
Hydrogen. 5.39 5.66 
Oxygen. 31.28 31.32 
This corresponds with the composition of oxytoluic acid, C 8 H 8 0 3 , 
which contains 63.15 per cent of carbon, 5.26 per cent of hydrogen, and 
31.50 per cent of oxygen. There are 10 isomeric oxytoluic acids, all of 
which have been described. The compound obtained from the soil has 
the properties of metaoxytoluic acid, with the carboxyl, hydroxyl, and 
methyl radicals in the 1. 3. 5. positions, respectively. 
This compound crystallizes in plates or, when the quantity is small, in 
groups of radiating needles. It is rather soluble in cold water, but more 
so in hot water. It is soluble in alcohol and ether, sublimes unchanged, 
and melts at 208° C. On the addition of a solution of ferric chlorid, an 
aqueous solution of the compound gives a brown precipitate which dis¬ 
solves to a brown solution when the reagent is added in excess. On the 
distillation of the dry compound with lime, metacresol is formed. The 
identity of the metacresol obtained from the soil compound in this way 
was established by transforming it into 2. 4. 6. trinitrocresol, a yellow com¬ 
pound melting at 106° to 107° C. This was effected by dissolving the 
metacresol in strong sulphuric acid, pouring into a mixture of nitric and 
sulphuric acids, heating, and then cooling. The nitro product was fil¬ 
tered off, washed with dilute hydrochloric acid, recrystallized, and dried. 
Metaoxytoluic acid was made from sulphotoluic acid according to the 
method of Jacobsen, 1 and its properties were compared with the com¬ 
pound obtained from the soil, the two agreeing in every respect. When 
the artificial product and the soil compound were mixed, the melting 
point was unchanged. The agreement in composition and properties 
mentioned is sufficient to establish the identity of the compound obtained 
from the soil as metaoxytoluic acid. 
VANILLIN 
In the course of investigations of the organic matter of soils carried on 
for the past six years soil extracts having the odor of vanillin and giving 
some of the reactions of that compound have been encountered from time 
to time, but its presence could not be confirmed by isolation in pure 
form. In investigating the soil samples from Florida the isolation was 
accomplished. 
The method of isolation, as with the compounds just described, was 
begun by making an alkaline extract of the soil. This extract was acidi¬ 
fied and filtered and was then shaken out with several portions of ether. 
1 Jacobsen, Oscar. Oxytoluylsauren und Oxyphtalsauren. Ber. Deut. Chem. Gesell., Jahrg. 14, Juli- 
Dez., p. 2357-2359,1881. 
