Hexamethylenetetramine → Benzoic acid, 3-formyl-4-hydroxy-, methyl ester

Participants

Reaction Steps

Methyl 4-hydroxybenzoate (1.52 g) is dissolved in trifluoroacetic acid (20 ml), thereto is added hexamethylenetetramine (700 mg) and the mixture is heated under reflux for 2 hours. The reaction solution is concentrated under reduced pressure, thereto is poured ice-water, and then the mixture is extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate and the solvent is evaporated under reduced pressure. The resulting residue is dissolved in chloroform, and then filtered to remove the insoluble materials. The filtrate is concentrated under reduced pressure, and then purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1) to give the title compound (540 mg).

Provenance & Evidence