Methyl morpholine oxide → HCID 57443292, compound

Participants

Reaction Steps

To a solution of 2-allyl-4-methyl-benzoic acid methyl ester (0.980 g, 5.15 mmol) in acetone (20 mL) and water (2.0 mL) are added N-methyl morpholine oxide (0.89 g, 7.57 mmol) and OsO4 (1 mg). The resulting reaction mixture is stirred at room temperature for three hours. The reaction mixture is diluted with ethyl acetate (50 mL) and is washed with Na2S2O3 (1.0 M, 20 mL). The organic layer are concentrated and the residue is dissolved in THF (25 mL) and water (15 mL). To the solution, NaIO4 (3.24 g, 15.2 mmol) is added and the mixture is stirred at room temperature for two hours. The mixture is filtered and the filtrate is concentrated, diluted with ethyl acetate (60 mL), and washed with Na2S2O3 (1.0 M, 20 mL). The organic layer is dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue is purified via flash chromatography eluting with 30-40% ethyl acetate in hexane to give the title compound (0.260 g, 26%). 1H NMR (400 MHz, CDCl3) δ 9.74 (s, 1H), 7.94-7.92 (d, 1H), 7.15-7.13 (d, 1H), 7.00 (s, 1H), 3.99 (s, 2H), 3.81 (s, 3H), 2.35 (s, 3H).

Provenance & Evidence