5.2 VI. -Preliminztry Note concernirJg a new Homolope of Benzoic Acid. BY ARTHURH. CHURCH,B.A. ATTEMPTS have been made to effect the oxidation of beuxol by means of an oxidizing mixture consisting of bicliromate of potassium and sulphuric acid; it has been found however that the hydrocarbon remained matt acked. Not so however with the other members of the same series toluol and cumol yielding benzoic acid and cymol an acid of totally different properties and constitution. I have succeeded in producing from benzol an apparently new oxygenated body presenting all the properties one might expect to find in a homologue of benzoic acid containing CH less than that substance. This supposition is strengthened by the result of ail experiment in which nitrobenzol was made to yield an acid body appreiitly standing in the same relation to the first-mentioned new acid as nitrobenzol to benzol.The following was the plan pursued in the preparation of the nem acids Pure benzol was dissolved in a slight excess of Nord-hausen sulphuric acid and the mixture heated for some time to 100°C. Itwas then diluted with about its bulk of water and transferred to a retort. Small fragments of bichromate of potassium were added gradually to the liquid the temperature of which was slowly raised. The acid was found partly floating on and partly dissolved in the aqueous distillate. Great care must be taken lest the oxidation proceed too actively and the product be lost. The acid is a white fusible and crystalline solid dis- tinguished €rom Collinic acid to which the same formula has been assigned by its far greater solubility in hot water.The analytical results indicate the formula- C6H402*for the acid; and C6H,M0 for the salts. The fact that benzol is reproduced in large quantity from sulphobenzolate of ammonium C6H,. NH,. SO, when that salt is submitted to dry distillation suggested the probability that the * C = 12; 0 =16; f3 = 32;H = 1. CHURCH ON A NEW HOMOLOGUE OF RENZOiC ACID. 53 acid itself when acted on by an oxidizing agent might yield the products which we should expect to obtain by the oxidation of the original benzol. When sulphotoluolic and sulphocumolic acids are similarly treated benzoic acid is the corresponding product with sulpho- cymolic acid a white powder apparently identical with the insolinic acid of Hofrnann is obtained.Nitrobenzol is attacked with the utmost difficulty by the chromic acid mixture. By long boiling it is however at length converted iiito a white acid which crystallizes from boiling water in large nacreous plates. Analysis has led to the formula- C,H,(N0,)02 for the acid ;an? C,H,(NO,)MO for the salts. Nitrotoluol and nitrocumol are oxidized with considerable ease under similar conditions yielding nitrobenzoic acid in abundance. This is the caw also with nitrosulphotoluolic acid C,HGNO,. €3’. SO, the acid sulpliite of nitrotoluenyl. The acid from nitrobenzol was obtained in June last but MM. CloGz and Mignet announce in the “Corriptcx Rendus” of January Zlst 1861 that they haw obtaieed a new acid from nitrobenzol by oxidizing it with permanganate of potassium or with a mixture of bichromate of potassium and nitric acid. To their acid they assign the espression C,H (NO,)O, But it is not easy to see how such a body can be derived from the oxidation of nitrobenzol which contains only C,. Indeed the authors are by no means certain of the purity of the nitrobenzol which they employed and they even go so far as to suggest that the acid which they describe may have owed its origin to some foreign body with which the commercial nitrobenzol on which they operated may have been contaminated.