Potassium Carbonate → 2-Chloro-4-[2-(dimethylamino)ethoxy]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-chloro-4-hydroxybenzaldehyde (234 mg, 1.49 mmol), (2-chloroethyl)dimethylamine hydrochloride (536 mg, 3.72 mmol), potassium carbonate (514 mg, 3.72 mmol), and tetrabutylammonium iodide (55 mg, 0.15 mmol) in 4.0 mL of acetonitrile was stirred at 115° C. overnight in a sealed tube. After the reaction mixture was diluted with water, the solution was extracted with ethyl acetate. The extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (chloroform/methanol=99/1 to 94/6) to obtain the title compound as a brown oil (137 mg, 40%).

Provenance & Evidence