5-Nitrofurfural → 2-(4-Benzyloxyphenyl)-3-(5-nitro-2-furyl)acrolein

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Reaction Steps

6.4 g of 1-(4-benzyloxyphenyl)-2-methoxyethylene, diluted with 10 cc of benzene, are added dropwise at 0°-5° to 11.15 g of 5-nitrofuran-2-aldehyde in 30 cc of dry benzene after the addition of a few drops of diethyl ether/trifluoroborane. The mixture is stirred at 40° for 11/2 hours, is washed with a 5% aqueous sodium acetate solution and with water, dried with magnesium sulphate and concentrated by evaporation. The residue is heated to 90° for 4 hours with 10% hydrochloric acid and glacial acetic acid. The mixture is again concentrated by evaporation, is taken up in ether and the acid salt portion is filtered off. After concentration, orange crystals having a M.P. of 145°-155°, crystallize from the ether solution.

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