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

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Reaction Steps

Methyl 4-hydroxybenzoate (1.52 g) is dissolved in trifluoroacetic acid (20 ml), and thereto is added hexamethylenetetramine (700 mg). The mixture is heated under reflux for 2 hours. The reaction solution is concentrated under reduced pressure, and thereto is poured ice-water. The mixture is then extracted with ethyl acetate. The organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is dissolved in chloroform, and filtered to remove the insoluble materials. The filtrate is concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1) to give the title compound (540 mg). ESI-MS M/Z:179[M−H]−

Provenance & Evidence