Methyl iodide → Methyl 3-hydroxy-5-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl 3,5-dihydroxybenzoate (89 mmol, 15 g), potassium carbonate (107 mmol, 14.79 g) and iodomethane (89 mmol, 5.55 ml, 12.66 g) in acetone (300 ml) was stirred at 60° C. for 4 hours. TLC showed a mixture of 3 compounds which were starting material, mono methylated product and demethylated product. After cooling to room temperature, acetone was removed under reduced pressure and the oily residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product was purified using normal phase chromatography was purified using normal phase chromatography eluting with ethyl acetate and increasing amounts of heptane to give methyl 3-hydroxy-5-methoxybenzoate (6.25 g) as a clear oil.

Provenance & Evidence