Water → 3-(Benzyloxy)-5-methylphenol

Participants

Reaction Steps

Orcinol monohydrate (7.10 g, 50 mmol) in DMF (20 mL) was added dropwise to NaH (95%, 2.4 g, 100 mmol) in DMF (60 mL). The reaction mixture was stirred at room temperature for 20 min. Benzyl bromide (8.55 g, 50 mmol) in DMF (20 mL was then added dropwise and the reaction mixture was stirred at room temperature for 2 h. Water (100 mL) was added slowly followed by extraction with ethyl acetate (3×100 mL). The organic phase was washed with brine (2×50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was then purified by flash column chromatography (3:1 hexane:ethyl acetate) to give the title compound as a yellow oil (3.15 g, 31%). 1H-NMR (300 MHz, CDCl3) 2.26 (s, 3H), 4.99 (s, 2H), 5.25 (s, 1H), 6.26 (s, 1H), 6.29 (t, 1H), 6.40 (s, 1H), 7.39 (m, 5H).

Provenance & Evidence