Potassium Carbonate → 2-Methoxy-6-(3-methoxyphenyl)naphthalene

Participants

Reaction Steps

A mixture of a mixed solvent (toluene/ethanol/water=2.5/2.5/1; 500 ml), the compound (T-2) (48.6 g, 319.6 mmol), 2-bromo-6-methoxynaphthalene (42.9 g, 181.0 mmol), 5% palladium on carbon (2.15 g), potassium carbonate (37.5 g, 271.5 mmol) and tetrabutylammonium bromide (14.6 g, 45.3 mmol) was refluxed with stirring for 15 hours under an atmosphere of nitrogen. The resulting reaction mixture was extracted with toluene (300 mL) three times, and the organic layer was washed with water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: toluene), and then by recrystallization from a mixed solvent of heptane, methanol and ethyl acetate to give colorless crystals (45.0 g) of 2-methoxy-6-(3-methoxyphenyl)naphthalene (T-9).

Provenance & Evidence