[5] Ber. 24, 2623 (1891)
[6] Ber. 29, 704 (1896)
Of the above methods, the only ones which need be considered are those in which a mixture of aniline, glycerol and sulfuric acid is heated with an oxidizing agent. With the use of nitrobenzene, the reaction, according to the original method, takes place with extreme violence.
The method above described is the most satisfactory for the preparation of quinoline itself, but for the preparation of homologues of quinoline, the use of arsenic acid is preferable, since the yields are somewhat greater.
Since the work was carried out, a method has been published[7] in which aniline, glycerol and sulfuric acid are treated with ferric oxide. By this method Adams and Parks were unable to obtain yields comparable with those resulting from the above directions.
[7] Chem. News 121, 205 (1920).
XXII
QUINONE
(1)HOC6H4OH(4) + O(Na2Cr2O7 + H2SO4)—> O=C6H4=O + H2O Prepared by E. B. VLIET. Checked by ROGER ADAMS and E. E. DREGER.
1. Procedure