Acetic Acid → 1,4-Naphthalenedione, 2,3-dimethoxy-5-nitro-

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Reaction Steps

A solution of 2,3-dichloro-5-nitro-1,4-naphthoquinone (8, 2.72 g, 10 mmol) in anhydrous tetrahydrofuran (15 ml) is added to a solution of 1 N sodium methoxide (25 ml, 25 mmol) and the resulting solution stored at 22° for 16 hours. Acetic acid (1 ml) is then added, the solution concentrated in vacuo and the residue partitioned between water (50 ml) and chloroform (100 ml). The aqueous phase is further extracted with chloroform (2×50 ml). The combined chloroform extracts are dried with MgSO4 and concentrated in vacuo. The residue is recrystallized from methanol giving 1.99 g (76%) of 10 FIG. 3a (R1 =R2 =OCH3) with mp 156°-157°.

Provenance & Evidence