Acetone → 1,7-Dimethoxynaphthalene

Participants

Reaction Steps

To one liter of acetone were added 50.0 grams (0.31 mole) of 1,7-dihydroxynaphthalene. To the solution then were added 95.0 gm (0.69 mole) of powdered potassium carbonate and 65 mL (0.69 mole) of dimethyl sulfate. The reaction mixture was stirred at reflux under nitrogen for 18 hours. The reaction mixture then was cooled to room temperature and diluted with 2 L of water. The mixture was then extracted with dichloromethane. The organic extracts were combined, washed successively with water and saturated aqueous sodium chloride, dried over sodium sulfate and evaporated in vacuo to give a brown oil. The oil was distilled in vacuo to give 52.51 gm (90.1%) of 1,7-dimethoxynaphthalene as a light orange, transparent oil, b.p.=115°-157° C. (4 mm Hg).

Provenance & Evidence