Hydrochloric Acid → Benzoic acid, 3-formyl-4-hydroxy-, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 4-hydroxybenzoate (20 g, 131 mmol) and methanesulfonic acid (80 mL), hexamethylenetetramine (20 g, 144 mmol) was added in small portions at room temperature. After stirring at 100° C. for 3.5 hours, concentrated hydrochloric acid (10 mL) and water (300 mL) were added. The reaction mixture was extracted twice with ethyl acetate and the organic phase was dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20-65:35) to give methyl 3-formyl-4-hydroxy-benzoate (7.24 g, 31%, mp 87.5-89.0° C.) as a colorless powder.

Provenance & Evidence