Hydrochloric Acid → Benzyl 3-hydroxyphenyl ether

Participants

Reaction Steps

3-Benzyloxyphenyl acetate (4.84 g, 20 mmol), as prepared in the preceding step, in tetrahydrofuran (50 mL) was treated with 1 N NaOH (30 mL) at room temperature for 3 h. The mixture was acidified with 1 N HCl and extracted with ethyl acetate (3'100 nmL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. The solvent was removed in vacuo and the residue purified by flash column chromatography (methylene chloride) to give the title compound as a colorless liquid (3.80 g, 96%). 1H-NMR (300 MHz, CDCl3) δ 5.01 (s, 2 H), 5.09 (s, 1 H), 6.47 (t, 2 H, J=2.2 Hz), 6.56 (dd, 1 H, J=1.1, 4.1 Hz), 7.11 (t, 1 H), and 7.39 (m, 5 H).

Provenance & Evidence