Methanol → Methyl 3-formylbenzoate

Participants

Reaction Steps

3-Formylbenzoic acid (3.11 g, 20.7 mmol, Aldrich) in 10:1 methanol:water (110 mL) was treated with Cs2CO3 (3.11 g, 10.4 mmol). After stirring 18 hours, the solvent was evaporated under reduced pressure and the residue was dried under reduced pressure at 60° C. The residue was suspended in DMF (40 mL) and treated with iodomethane (2.58 mL, 41.4 mmol). After stirring at ambient temperature 2 hours, the mixture was poured into water and extracted with diethyl ether. The ether extracts were combined, washed with water, saturated NaHCO3, dried (MgSO4), filtered and the filtrate concentrated under reduced pressure to provide the title compound as a white solid (2.81 g).

Provenance & Evidence