A Schlenk flask was charged with 6-methoxy-3,4-dihydronaphthalen-1(2H)-one (1,352 mg, 2.0 mmol), sodium tert-butanolate (365 mg, 3.8 mmol) and Pd-132 (1.4 mg, 0.002 mmol). The flask was sealed with a rubber stopper, evacuated three times and backfilled with nitrogen operation. Chlorobenzene (0.20 mL, 2.0 mmol) was added to the flask via a gas-tight syringe, followed by dioxane (2.0 mL). The reaction mixture was stirred at 100°C for 18 hours. After completion of the reaction, the mixture was filtered through a silica gel column and the silica gel pad was washed with methyl tert-butyl ether (MTBE, 20 mL). The filtrate was concentrated to give the off-white solid product 6-methoxy-2-phenyltetralone (455 mg, 90% yield). The structure of the product was confirmed by 1H NMR (CDCl3) and 13C NMR (CDCl3).
