4-Methoxy-1-naphthol → 4,4-dimethoxy-4H-naphthalen-1-one

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Reaction Steps

For example, a solution of 4-methoxynaphthol (16 mmol) and iodobenzene diacetate (6.1 g, 19 mmol) in methanol (75 mL) is stirred at room temperature, under a nitrogen atmosphere for 1 hour. The resultant dark blue solution is poured into a saturated solution of NaHCO3 (75 mL), then evaporated to reduced volume. The blue oil is extracted with CH2Cl2 (3×75 mL) and the organic layer is washed with water (3×75 mL), brine (2×75 mL), and is dried over MgSO4, and filtered and evaporated to dryness (bath temp. <40° C.) to yield the product as a dark blue semi-solid.

Provenance & Evidence