Hydrochloric Acid → 3-[Hydroxy(1-nitronaphthalen-2-yl)methyl]benzonitrile

Participants

Reaction Steps

To a solution of bis(2-dimethylaminoethyl)ether (5.62 mL, 29.8 mmol) in THF (125 mL) was added a solution of 2M isopropylmagnesium chloride in THF (14.9 mL, 29.8 mmol) dropwise under N2 atmosphere at room temperature, and stirred for 20 min. To the mixture was added 3-iodobenzonitrile (5.69 g, 24.9 mmol), and stirred for 30 min. To an ice-cold solution of the resultant mixture was added 1-nitro-2-naphthaldehyde, and stirred at room temperature for 1 hour. To the reaction mixture was poured 1M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1), to give the titled compound as a green orange oil (7.37 g, yield 97%).

Provenance & Evidence