Methyl iodide → 4-Benzyloxy-2-methoxybenzoic acid methyl ester

Participants

Reaction Steps

To a stirred, 0° C. solution of methyl 4-benzyloxy-2-hydroxybenzoate (12g, 46 mmol) from step 1 above in DMF (150 mL) was added NaH (2.76 g of a 60% suspension in mineral oil, 69 mmol) and methyl iodide (7.2 mL, 116 mmol). The solution was warmed to ambient temperature and stirred for 18 h. The reaction mixture was poured onto ice and the resulting solution was extracted with ether (3×200 mL). The organic phase was dried (MgSO4), filtered and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 4:1 hexanes:EtOAc as eluant. Methyl 4-benzyloxy-2-methoxybenzoate was obtained as a white powder.

Provenance & Evidence