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

Beteiligte Stoffe

Reaktionsschritte

A solution of 4-methoxy-1-naphthol (2.76 g, 15.8 mmol) and DAIB (6.10 g, 18.9 mmol) on methanol (75 mL) was stirred at 25° C. under a nitrogen atmosphere for 1 h. The resultant dark blue solution was poured into a saturated NaHCO3 (aq) solution (75 mL), then the mixture concentrated to approx. 50 mL in vacuo. The blue oil was extracted with dichloromethane (3×75 mL) and the organic layer washed with water (2×75 mL) and brine (2×75 mL), then dried (MgSO4), filtered and concentrated in vacuo (water bath temperature <40° C.) to yield 4,4-dimethoxy-4H-naphthalen-1-one as a dark-blue semi-solid which was used without further purification; 1H NMR (CDCl3) δ 8.15 (1H, d, J 8.0 Hz, ArH), 7.40–7.85 (3H, m, ArH), 6.90 (1H, d, J 12.2 Hz, H-3), 6.55 (1H, d, J 12.2 Hz, H-2), 3.15 (6H, s, OCH3).

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