Chemistry of quinones. Part 6. The selective hydrolysis of α-acetoxyanthraquinones and related compounds by trifluoroacetic acid containing small amounts of water

Abstract

Acetoxy- or benzoyloxy-substituents adjacent to the carbonyl groups of anthraquinone, 1,4-naphthoquinone, naphthacene-5,12-quinone, benzophenone, and methyl benzoate are selectively converted into hydroxy-groups by treatment with trifluoroacetic acid containing small amounts of water. In the absence of water a reversible acidolysis occurs. Water reacts with the acylating agent, thus preventing the reverse reaction. Evidence is presented that the hydrolyses are of the A_AC1 type.