Methanol → 4-Carbamoylbenzoic acid

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Reaction Steps

LiOH (26 mg, 0.6 mmol) was added to a stirred solution of terephthalamic acid methyl ester (73 mg, 0.41 mmol) in THF:MeOH:water mixture (3:1:1, 1 mL) and the resulting mixture was stirred at room temperature overnight. The THF and MeOH were then evaporated and the resulting residue was acidified to pH 2 using 10% citric acid solution. The product was extracted using EtOAc. The organic layer was washed with saturated brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford 30 mg (53.6% yield) of terephthalamic acid. LCMS Purity: 92.2%.

Provenance & Evidence