Anthraquinone dyes. Part IV. Nitration of 2-(3-chloro-4-methyl-benzoyl)benzoic acid

Abstract

The principal product of the nitration of 2-(3-chloro-4-methylbenzoyl) benzoic acid is 2-(3-chloro-4-methyl-6-nitrobenzoyl)benzoic acid, formed in 70--80% yield. In addition, 10-1 5% of 2-(3-chloro-4-methyl-2-nitro-benzoy1)-and 2-(3-chloro-4-methyl-5-nitrobenzoyl) -benzoic acid are formed. This result is in disagreement with a semiquantitative estimate, based on sigma constants, from which 2-(3-chloro-4-methyl-5-nitrobenzoyl)benzoic acid would be the principal reaction product expected. in a study of the nitration of 2-(3-chloro-4-methylbenzoyl) benzoic acid, authentic specimens of 1,4-dichloro-2-methyl-, 1,2-dichloro-3-rnethyl-, and 2.3-dichloro-1 -methyl-derivatives of anthraquinone were prepared.

The Ortho Effect on the Acidic and Alkaline Hydrolysis of Substituted Formanilides

“…Ionization constants (pK a ) were determined for the carboxyland hydroxyl-substituted formanilides using potentiometry (p-hydroxy (9.58)) and UV spectroscopy (pcarboxyl (4.02), m-carboxyl (3.86), o-carboxyl (3.37), m-hydroxyl (9.59), and o-hydroxyl(8.98)) [21,22]. The compounds had melting points and NMR spectra in good agreement with literature values [6,9,[23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39]. The spectra of the compounds not previously synthesized are reported below.…”