Oxygen → Methyl 4-formyl-2-hydroxybenzoate

Beteiligte Stoffe

Reaktionsschritte

A steady stream of O2 (g) is passed through a cold (−78° C.) solution of 2-hydroxy-4-vinyl-benzoic acid methyl ester (3.28 g, 0.0184 mol) in CH2Cl2 (50 ml). After 5 minutes, O3 (g) is bubbled into the solution until the solution's color turns blue/gray. The solution is then purged with O2 (g) for 5 minutes, treated with DMS (4.05 ml, 0.0552 mol) and allowed to warm to room temperature overnight. All volatiles are removed in vacuo and the crude product is purified with silica gel column chromatography (0-100% ethyl acetate in hexanes gradient) to afford 4-formyl-2-hydroxy-benzoic acid methyl ester: ESMS m/z 181.0 (M+H+).

Herkunft & Nachweise