Conclusions.
In the course of this investigation several facts have been established.
1. By the methods described, the symmetrical chloride of paranitroorthosulphobenzoic acid can be obtained in fine crystalline form, perfectly free from its isomer, with an average yield of forty percent.2. By treatment of the chloride with benzene and aluminium chloride, only one chlorine atom can be replaced by a phenyl group.3. The barium salt of paranitroorthobenzoyl benzenesulphonic acid, when perfectly pure, crystallizes constantly with seven molecules of water of crystallization.4. With alcohols, the symmetrical chloride yields directly the acid etherial salt of paranitroorthosulphobenzoic acid, no evidence having been obtained of an intermediate chloro-etherial salt. The unsymmetrical chloride on the other hand yields the intermediate product.5. With phenols, two series of derivatives are obtained.(1) With monohydroxy phenols, both etherial salts and sulphonphthaleïns are formed, the former predominating.(2) With polyhydroxy phenols no etherial salts were obtained, but compounds of the unsymmetrical type, usually containing more than two phenol residues.6. With aniline an anil and an anilid of symmetrical constitution are formed.7. With phosphorus oxychloride, the anilid, by loss of water, forms a dianil.8. This dianil undergoes transformation with(1) Glacial acetic acid, forming an anilid of unsymmetrical constitution.(2) Hydrochloric acid forming the anil.(3) Alcoholic potash, with the formation of colored decomposition products.
1. By the methods described, the symmetrical chloride of paranitroorthosulphobenzoic acid can be obtained in fine crystalline form, perfectly free from its isomer, with an average yield of forty percent.
2. By treatment of the chloride with benzene and aluminium chloride, only one chlorine atom can be replaced by a phenyl group.
3. The barium salt of paranitroorthobenzoyl benzenesulphonic acid, when perfectly pure, crystallizes constantly with seven molecules of water of crystallization.
4. With alcohols, the symmetrical chloride yields directly the acid etherial salt of paranitroorthosulphobenzoic acid, no evidence having been obtained of an intermediate chloro-etherial salt. The unsymmetrical chloride on the other hand yields the intermediate product.
5. With phenols, two series of derivatives are obtained.
(1) With monohydroxy phenols, both etherial salts and sulphonphthaleïns are formed, the former predominating.(2) With polyhydroxy phenols no etherial salts were obtained, but compounds of the unsymmetrical type, usually containing more than two phenol residues.
(1) With monohydroxy phenols, both etherial salts and sulphonphthaleïns are formed, the former predominating.
(2) With polyhydroxy phenols no etherial salts were obtained, but compounds of the unsymmetrical type, usually containing more than two phenol residues.
6. With aniline an anil and an anilid of symmetrical constitution are formed.
7. With phosphorus oxychloride, the anilid, by loss of water, forms a dianil.
8. This dianil undergoes transformation with
(1) Glacial acetic acid, forming an anilid of unsymmetrical constitution.(2) Hydrochloric acid forming the anil.(3) Alcoholic potash, with the formation of colored decomposition products.
(1) Glacial acetic acid, forming an anilid of unsymmetrical constitution.
(2) Hydrochloric acid forming the anil.
(3) Alcoholic potash, with the formation of colored decomposition products.