A New Synthesis of 3-Hydroxy-2, 5-dialkyl-1, 4-benzoquinone from 3-Halo-3, 6-dialkyl-1, 2-cyclohexanedione Using Iodine–Copper (II) Acetate

CA Horiuchi, Y Suzuki

Index: Horiuchi; Suzuki Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 9 p. 2919 - 2922

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Citation Number: 7

Abstract

The reaction of 3-iodo-3, 6-dialkyl-1, 2-cyclohexanedione (2) with iodine–copper (II) acetate in acetic acid–water (5: 1) at 80° C gave the respective 3-hydroxy-2, 5-dialkyl-1, 4- benzoquinone in 38–80% yields. On the other hand, the reaction of 2 with copper (II) acetate in acetic acid–water (10: 1) under refluxing afforded the respective 3, 3′-dihydroxy 2, 2′, 5, 5′-tetraalkyl-4, 4′-diphenoquinone (5) in 41–85% yields. In the case of 3-bromo-3, 6- ...