Potassium Carbonate → HCID 17985754, compound

Participants

Reaction Conditions

Reaction Steps

Add bromoacetaldehyde dimethylacetal (30.3 g, 179 mmol) to 2-methyl-5-nitrophenol (25 g, 163 mmol) and potassium carbonate (50 g, 362 mmol) in dimethylformamide (200 mL). Stir the mixture and reflux under nitrogen for 2.5 hours. Cool the mixture to 20° C. and add aqueous sodium hydroxide (200 mL, 1 M). Dilute the mixture with hexane and diethyl ether (1:1), then wash with 0.2M aqueous sodium hydroxide and aqueous saturated sodium chloride. Dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Precipitation of the product from hexane gives 30.6 g (77%) of the title compound, as a tan colored solid. 1H NMR (400 MHz, CDCl3) δ 7.78 (dd, 1 H, J=8.4, 2.4 Hz), 7.66 (d, 1 H, J=2.4 Hz), 7.26 (dd, 1 H, J=8.4, 0.8 Hz), 4.76 (t, 1 H, J=4.8 Hz), 4.09 (d, 2 H, J=35.2 Hz), 3.48 (s, 6 H), 2.32 (s, 3 H).

Provenance & Evidence