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) (2.00 g, 5.43 mmol) in MeOH (40 mL) were added an aqueous solution of, 30-40% by weight, H2O2 (5.0 mL) and a few drops (10-12) of conc. H2SO4. The resultant mixture was stirred for 24 h. Reaction mixture was neutralized with saturated aqueous NaHCO3 and then diluted with EtOAc (200 mL). Reaction mixture was washed with water (2×30 mL), brine (1×30 mL), 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 1.180 g (61%) of the title compound (233) as a white foam. The 1H NMR and mass spectral data are consistent with the data reported in Example 41 (Step 1).

Provenance & Evidence