Methanol → Methyl 5-Formylsalicylate

Participants

Reaction Steps

Heat a mixture of 5-formyl-2-hydroxy-benzoic acid (5.0 g, 30.09 mmol) concentrated sulfuric acid (5 mL) in methanol (100 mL) at reflux for 24 h. Cool the mixture to room temperature and concentrate under reduced pressure. Purify the resulting residue by chromatography over silica gel, eluting with hexanes/ethyl acetate (80:20), to provide the title compound as a colorless oil (4.28 g, 79%). 1H NMR (CDCl3, 300 MHz) δ 3.88 (s, 3H), 4.52 (bs, 1H), 7.05 (d, J=8.56 Hz, 1H), 7.84 (d, J=8.56 Hz, 1H), 8.40 (s, 1H), 9.85 (s, 1H); TLC Rf=0.34 (3:1 Hexanes/Ethyl Acetate).

Provenance & Evidence