4-Chlorobenzaldehyde → HCID 13392574, compound

Participants

Reaction Steps

A mixture of 25 g of 2-methyl-5-pyridinol, 32 g of 4-chlorobenzaldehyde, 75 g of potassium carbonate and 200 ml of dimethylformamide was heated under refluxing for 6 hours with stirring. After cooling, the mixture was filtered and the filtrate was concentrated. The resulting oily substance was dissolved in diethyl ether, and the solution was washed successively with an aqueous solution of sodium hydroxide and water, and dried over magnesium sulfate. The solvent was then distilled off and the resulting oily substance was dissolved in isopropyl alcohol. To the solution was added concentrated hydrochloric acid, and the resulting hydrochloride was filtered and recrystallized from a mixture of methanol and ethyl acetate to obtain colorless needles. The crystals were added to an aqueous solution of sodium carbonate and the mixture was extracted with dichloromethane. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off to obtain an oily substance which crystallized upon standing. The crystals were recrystallized from hexane to obtain 17 g (35% yield) of 4-(2-methyl-5-pyridyloxy)benzaldehyde as colorless prisms having a melting point of 45°-46° C. and a boiling point of 133° C./2 mmHg (bath temperature).

Provenance & Evidence