4-Fluoro-3-phenoxybenzaldehyde → (4-Fluoro-3-phenoxyphenyl)methanol

Participants

Reaction Steps

Under argon 2.16 g (0.010 mole) of 4-fluoro-3-phenoxybenzaldehyde was dissolved in 50 ml of absolute ethanol. To this solution was added with stirring 0.28 g (0.0074 mole) of sodium borohydride. After stirring at room temperature for 24 hours, 3 ml of 10% hydrochloric acid was added to the reaction mixture. The solvent was then evaporated under reduced pressure, leaving a milky-white residue. This residue was dissolved in 100 ml of diethyl ether and 5% hydrochloric acid. The organic phase was separated, washed in succession twice with 25 ml of 5% hydrochloric acid and twice with 10 ml of a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, leaving 1.98 g of (4-fluoro-3-phenoxyphenyl)methyl alcohol as a clear, colorless liquid. The nmr and ir spectra were consistent with the proposed structure.

Provenance & Evidence