Methanol → Methyl 4-(4-pyridinyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[pyridin-4-yl]-benzoic acid (2.0 g, 10 mmol) (reference example 11a) in methanol (30 mL) is added conc. H2SO4 (4 mL). The resulting solution is warmed to 60° C. and stirred at this temperature for 2.5 hours. The reaction mixture is then allowed to cool to room temperature then poured into ice. The pH of the resulting solution is adjusted to 7 using a 10 M solution of NaOH. The product is then extracted into ethyl acetate. This solution is washed with brine, dried over MgSO4 and concentrated to give 2.1 g of the title compound as a white solid. 1H NMR (CDCl3) d 3.94 (s, 3H), 7.50 (d, J=5 Hz, 2H), 7.69 (d, J=8 Hz, 2H), 8.13 (d, J=5 Hz, 2H) 8.68 (d, J=5 Hz, 2H). MS (EI) m/z 213 (M)+.

Provenance & Evidence