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

Participants

Reaction Steps

To a suspension of 4-[pyridin-4-yl]-benzaldehyde (approx. 2.8 g, 15 mmol) (reference example 8a) in t-butanol (100 mL) was 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 was stirred for 20 min then the precipitated solid filtered off. This solid was washed with water then set aside. The organic phase of the mother liquor was separated then washed with brine, dried over MgSO4 and concentrated to give a solid. This material was 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)+.

Provenance & Evidence