4-Methoxybenzoic Acid → 4-Methoxybenzoic Acid

Participants

Reaction Steps

To prepare 4-methoxybenzoic acid, 4-methoxybenzaldehyde (100 mg) was dissolved in DMF (10 mL), and OXONE (0.451 g) was added and stirred at room temperature for 3 hours with the reaction having a final volume (11 mL). The reaction was monitored by TLC or GC analysis. EtOAc was added to extract the products and 1N HCl was used to dissolve the salts. The organic extract was washed with 1N HCl (30 mL×3) and brine (30 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 4-methoxybenzoic acid in 31% yield and 4-methoxyphenol formate in 58% yield after purification by silica gel column chromatography. 4-Methoxyphenyl Formate: 1H NMR (CDCl3, 300 MHz): δ8.26 (s, 1H), 7.03 (d, 2H, J=9.0), 6.89 (d, 2H,J=8.9), 3.78 (s, 3H); 13C NMR (CDCl3, 75 MHz): 8176.7, 170.5, 79.9, 74.3, 31.4, 30.4, 28.2, 24.8, 23.9, 22.4, 20.9, 13.9.

Provenance & Evidence