Potassium Carbonate → 4-[4-(1H-imidazol-1-yl)phenoxy]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A suspension of 40.04 g (0.25 mole) of 4-(1H-imidazol-1-yl)phenol, 15.2 g (0.11 mole) of anhydrous potassium carbonate, 1 g of copper-I-bromide, and 0.5 g of activated copper powder in 100 ml of anhydrous dimethyl formamide was heated to 90° C. Over the course of 7 hours 47.03g (0.25 mole) of 4-bromobenzaldehyde were added in small portions to the suspension while the mixture was heated to 140° to 145° C. After the addition of the aldehyde was completed, the mixture was allowed to cool. Then 1500 ml of ice-cooled ethyl acetate were added to the reaction mixture. The resulting mixture was shaken with 500 ml of 1N aqueous sodium hydroxide solution. After separation of undissolved ingredients, the organic layer was shaken with 1N aqueous sodium hydroxide solution and washed with a saturated aqueous sodium chloride solution. After drying over magnesium sulfate, the drying agent was separated and the resulting filtrate evaporated at 45° C. and 2.6×103 to 6×103Pa. After column chromatography with ethyl acetate, 37.37 g (56.6% of the theoretical yield) of the aldehyde were obtained in the form of yellow brown crystals melting at 120° to 121° C.

Provenance & Evidence