4-Hydroxybenzyl Alcohol → Acetic acid, [4-(hydroxymethyl)phenoxy]-, ethyl ester

Participants

Reaction Steps

To a 500 mL round bottomed flask with a stirring bar and an argon inlet was added 4-hydroxybenzyl alcohol (7.50 g, 60.42 mmol), Cs2CO3 (29.53 g, 90.63 mmol), DMF (100 mL), and ethyl bromoacetate (11.09 g, 66.46 mmol). This mixture was stirred at ambient temperature for 2 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc and water. The layers were separated and the organic phase was washed with two additional portions of water. Drying (MgSO4), filtration and removal of the solvent in vacuo, gave an oil. This material was chromatographed on 250 g of silica gel using 1:1 EtOAc-hexane as eluant. There was obtained ethyl 2-(4-hydroxymethyl-phenoxy)acetate 35-4 (7.47 g, 59%) as an oil. 1H NMR (CDCl3): δ 1.29 (t, J=7 Hz, 3H), 2.07 (br s, 1H), 4.26 (q, J=7 Hz, 2H), 4.58 (s, 2H), 4.60 (s, 2H), 6.88 (d, J=9 Hz, 2H), 7.27 (d, J=9 Hz, 2H).

Provenance & Evidence