Water → 1,2-dimethoxynaphthalene

Participants

Reaction Steps

To the solution of 1,2-dihydroxynaphthalene (5 g, 31.2 mmol) in DMF (140 mL) was added NaH (3.0 g, 75.0 mmol). After stirred at room temperature for 1 h, dimethylsulfate (7.09 mL, 75.0 mmol) was added. After stirring at room temperature for 22 h, water and Et2O was added, the organic layer was washed with brine, water, dried (MgSO4), filtered and concentrated. Column chromatography yielded the title compound as a colorless oil (3.83 g, 65%). 1H NMR (CDCl3) δ 8.12 (d, 1H), 7.79 (d, 1H), 7.59 (d, 1H), 7.47 (m, 1H), 7.35 (m, 1H), 7.29 (d, 1H), 3.99 (s, 3H), 3.99 (s, 3H).

Provenance & Evidence