Summary
Reduction of anthraquinone, 2-methylanthraquinone, 2-mercaptomethylanthraquinone (I),bis-2-anthraquinonylmethyl sulphide (II) andbis-2-anthraquinonylmethyl disulphide (III) by Raney alloy in aqueous alkaline solution was studied. Anthraquinone gave 1:2:3:4-tetrahydroanthraquinone. When 2-methylanthraquinone was reduced with varying amounts of Raney alloy, several hydro derivatives of 2-methylanthraquinone were obtained. One was 1:2:3:4-tetrahydro-6-methylanthraquinone, the constitution of which was proved by oxidation to adipic and 4-methylphthalic acids. Desulphurization of (I) gave 2-methylanthraquinone, 2-hydroxymethylanthraquinone and anthraquinone-2-carboxylic acid; (II) gave 2-methylanthraquinone and traces of Anthraflavone; and (III) gave 2-methylanthraquinone, 2-hydroxymethylanthraquinone and anthraquinone-2-carboxylic acid. Anthraflavone gave decahydroanthraflavone as the major product and a small amount of 1:2:3:4-tetrahydro-6-methylanthraquinone.
Dehydrogenation of tetrahydro- and tetrahydromethylanthraquinones to the parent compounds was effected by several methods including treatment with iodine and sodium acetate in nitrobenzene and the action of activated alumina on a hexane solution. Treatment of tetrahydroanthraquinone with selenium dioxide at 170° gave a mixture of anthraquinone, α-hydroxyanthraquinone and quinizarin. Decahydroanthraflavone was dehydrogenated in two steps to Anthraflavone.
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Ramanathan, V., Tilak, B.D. & Venkataraman, K. Raney nickel reductions. Proc. Indian Acad. Sci. (Math. Sci.) 38, 161–175 (1953). https://doi.org/10.1007/BF03045217
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DOI: https://doi.org/10.1007/BF03045217