Hydrochloric Acid → 3-(2-Hydroxyethoxy)benzonitrile

Participants

Reaction Steps

2-(3-Cyanophenoxy)ethyl acetate (3.01 g, 14.7 mmol) obtained in Step 1 was dissolved in a mixed solvent of methanol and tetrahydrofuran (1:1), and 2N lithium hydroxide solution (14.7 ml) was added under ice-cooling. The mixture was stirred at room temperature for 45 min, 3N hydrochloric acid (10 ml) was added under ice-cooling, and the mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the mixture was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution, and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate 85:15-55:45) to give the title compound.

Provenance & Evidence