Dimethylformamide → Methyl 4-ethoxy-3,5-dimethoxybenzoate

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Reaction Steps

Combine methyl 3,5-dimethoxy-4-hydroxy-benzoate (2.12 g, 10 mmol) and dimethylformamide (50 mL). Cool in an ice bath. Add portionwise, sodium hydride (0.4 g, 16.7 mmol). after 2 hours, add iodoethane (4 mL, 50 mmol). Warm to ambient temperature. After 18 hours, dilute the reaction mixture with ethyl acetate and extract with water, 1M hydrochloric acid solution, a saturated sodium bicarbonate solution, and then brine. Dry the organic layer over MgSO4, filtered and evaporated in vacuo to give a residue. chromatograph the residue on silica gel eluting with 5% ethyl acetate/hexane to give methyl 3,5-dimethoxy-4-ethoxy-benzoate.

Provenance & Evidence