Methyl iodide → Methyl 5-formyl-2-methoxybenzoate

Participants

Reaction Steps

Methyl iodide (3.6 mL, 0.042 mol, 3.5 eq) was added dropwise to a stirred solution of 5-formylsalicylic acid (2.78 g, 0.017 mol, 1 eq) and cesium carbonate (16.36 g, 0.050 mol, 3 eq) in N,N-dimethylformamide (50 mL). The reaction mixture was stirred overnight, then diluted with ethyl acetate (100 mL) and the organic solution washed with water (100 mL), and brine (4×100 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to a cream coloured powder (2.8 g, 86%). 1H NMR (CDCl3) δ9.92 (s, 1H, O═C—H), 4.01 (s, 3H, CH3), 3.93 (s, 3H, CH3).

Provenance & Evidence