Hydrogen Peroxide → 4-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenol

Participants

Reaction Steps

To a solution of 4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}benzaldehyde (8) (0.740 g, 2 mmol) in MeOH (20 mL) were added an aqueous solution of 30-40%, by weight, H2O2 (0.60 mL) and 2-3 drops of conc. H2SO4. The resultant mixture was stirred for over night. The reaction mixture was neutralized with sat. NaHCO3 and then diluted with EtOAc (100 mL). The organic layer was washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure to afford the crude product. The product was purified by SiO2 column chromatography using hexanes:EtOAc (9:1 to 4:1) as an eluent to give 0.570 g (80%) of the title compound (233) as a white foam. IR (film) 3415, 1633, 1599, 1503, 1198 cm-1. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J=9.2 Hz, 1H), 7.53 (s, 1H), 7.29-7.22 (m, 3H), 7.14-7.11 (m, 3H), 7.08 and 7.03 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.53-6.50 (m, 2H), 6.45-6.42 (m, 2H), 3.93 (s, 3H), 2.23 (s, 3H). LCMS (ES) m/z 357.01 (M+H)+.

Provenance & Evidence