Methanol → 4-Ethynylbenzoic acid

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Reaction Steps

4-(Trimethylsilyl)ethynyl-benzoic acid methyl ester (714 mg, 3.07 mmol) was dissolved in 4% KOH:MeOH (w:v, 30 mL) and allowed to reflux overnight. The reaction was quenched with 6N HCl to pH 2-3 (as indicated by pH paper) and extracted 2× with EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and evaporated to afford 4-ethynylbenzoic acid (427 mg, 2.92 mmol, 95%) as a brown solid. H-NMR (d6-acetone, 500 MHz) δ (ppm): 7.62 (d, J=16.2 Hz, 2H); 8.03 (d, J=16.3 Hz, 2H).

Provenance & Evidence