Water → (4-Fluoro-2-methylphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

4-Fluoro-2-methylbenzoate (15.3 g, 91 mmol) was dissolved in THF under a stream of nitrogen. The mixture was cooled to 0° C. while adding LiAlH4 (4.4 g, 110 mmol) in small portions and then stirred at room temperature for 1 h. Water (4.4 mL), aqueous 15% NaOH (4.4 mL) and then more water (13.2 mL) were added dropwise in the given order while cooling to 0° C. The mixture was stirred for 2 h and then the solid material was filtered off. The solvent was removed by evaporation and there was obtained 11.5 g (90%) of (4-fluoro-2-methylphenyl)methanol as an oil. 1H NMR (300 MHz, CDCl3): 2.4 (s, 3H), 4.6 (s, 2H), 6.8-6.9 (m, 2H), 7.3 (t, 1H).

Provenance & Evidence