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Naphthalene-1,5-diol (16.0 g, 100 mmol) and potassium carbonate (27.6 g, 200 mmol) were stirred in acetone (300 mL) and dimethyl sulfate (32 mL) was added using syringe. The mixture was then heated to reflux under nitrogen overnight. Water (300 mL) was added after the mixture was cooled to room temperature. The precipitate was collected by filtration and washed with water (4×50 mL), then methanol (3×50 mL). After drying under vacuum, the solid was heated at reflux in ethanol (300 mL) for 2 hours. After cooling to room temperature, the desired product was then collected by filtration to give a pale brown solid (17.9 g, 95.2%). 1H NMR (500 MHz, CDCl3): δ 7.45 (d, J=8.5 Hz, 2H), 7.33 (t, J=8.5 Hz, 2H), 6.83 (d, J=8.5 Hz, 2H), 4.00 (s, 6H).

1. temperatureThe mixture was then heated
2. temperatureto reflux under nitrogen overnight
3. filtrationThe precipitate was collected by filtration
4. washwashed with water (4×50 mL)
5. customAfter drying under vacuum
6. temperaturethe solid was heated
7. temperatureat reflux in ethanol (300 mL) for 2 hours
8. temperatureAfter cooling to room temperature
9. filtrationthe desired product was then collected by filtration