Sodium Methoxide → 6-Methoxy-3-methyl-2-phenyl-1-naphthol

Participants

Reaction Steps

To a solution of 3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl acetate (6) (4.00 g, 13.1 mmol) in THF and MeOH (200 mL, 1:1) was added sodium methoxide (26 mL, 0.5 M solution in MeOH) at room temperature. The reaction mixture was stirred for 3 h under N2. The reaction mixture was concentrated under reduced pressure to afford the crude product, which was purified by SiO2 column chromatography to afford 3.4 g (99%) of compound 7 as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.10 (d, J=8.0 Hz, 1H), 7.54 (dd, J1=12.0 Hz, J2=8.0 Hz, 2H), 7.45 (dd, J1=8.0 Hz, J2=8.0 Hz, 1H), 7.36 (d, J1=4.0 Hz, 2H), 7.23 (s, 1H), 7.10 and 7.08 (dd, J1=8.0 Hz, J2=4.0 Hz, 1H), 7.05 (d, J1=4.0 Hz, 1H), 5.21 (s, 1H), 3.93 (s, 3H), 2.18 (s, 3H).

Provenance & Evidence