Journal of the Chemical Society (Resumed)

335. The reduction of juglone

RH Thomson

Index: Thomson Journal of the Chemical Society, 1951 , p. 1237 Journal of the Chemical Society, 1952 , p. 1822

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Citation Number: 3

Abstract

The yellow compound previously obtained by hydrogenolysis of 3-carboxymethylthiojuglone (I; R= H) with Raney nickel is shown to be 5: 8-dihydroxy-1-tetralone (VI; R= H) arising by further reduction of a-hydrojugione (11). Similar treatment of P-hydrojuglone gives the keto- alcohol (IV). IN the preparation of plumbagin (2-methyljuglone) by hydrogenolysis of (I; R= Me) with Raney nickel, a small amount of a yellow by-product (A), mp 164", was isolated (J ...