2-Methyl-2-butene → 4-(Pyridin-4-yl)benzoic acid

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Reaction Steps

To a suspension of 4-[pyridin-4-yl]-benzaldehyde (approx. 2.8 g, 15 mmol) (reference example 12a) in t-butanol (100 mL) is added 2-methy-but-2-ene (15 mL) followed by a solution comprised of NaClO2 (14.7 g, tech.grade) and NaH2PO4.H2O (14.7 g, 105 mmol) in H2O (100 mL). This mixture is stirred for 20 minutes then the precipitated solid filtered off. This solid is washed with water then set aside. The organic phase of the mother liquor is separated, then washed with brine, dried over MgSO4 and concentrated to give a solid. This material is combined with the solid obtained by filtration and dried under vacuum to give 2.34 g of the title compound. 1H NMR (DMSO) d 7.77 (d, J=6 Hz, 2H), 7.93 (d, J=8 Hz, 2H), 8.06 (d, J=8 Hz, 2H), 8.70 (d, J=6 Hz, 2H). MS (EI) m/z 199 (M)+.

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