2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Hydroxy-7-methoxy-1-tetralone

Participants

Reaction Conditions

Reaction Steps

A solution of 231 mg of 2,3-dichloro-5,6-dicyanobenzoquinone in 2 mL of dioxane was added dropwise over a period of 3 minutes to a stirred solution of 89 mg of 6-hydroxy-7-methoxytetralin dissolved in 5% aqueous dioxane under an atmosphere of nitrogen. The resulting solution was stirred at 25° C. under nitrogen for 3 hours. Thereafter the reaction mixture was filtered through a sintered glass funnel and the solid residue of 2,3-dichloro-5,6-dicyanodihydrobenzoquinone was washed with 2 mL of dioxane. The residue wash solution was combined with the filtrate. Thereafter the dioxane was evaporated from the combined filtrate at reduced atmospheric pressure. The resulting residue was chromatographed on a column of silica gel eluted with a solution of ethyl acetate and hexane in ratio of 1 to 1 to obtain 68 mg of known 6-hydroxy-7-methoxytetralin-1-one having m.p. 117-119° C. (lit. 117-119° C. Grethe, G. et al J Org. Chem, 1968, 33 504-508.)

Provenance & Evidence