3-Hydroxybenzyl alcohol → [3-(2-Methoxyethoxy)phenyl]methanol

Participants

Reaction Steps

3-Hydroxybenzyl alcohol (3.76 g, 30 mmol), 2-bromoethylmethyl ether (8.0 ml, 85 mmol) and cesium carbonate (14.7 g, 45 mmol) were heated at 60° C. for 3 h. The reaction was diluted with water, extracted (3×) with ethyl acetate and dried over sodium sulfate. The solution was filtered, concentrated and purified by silica chromatography (DCM followed by DCM/MeOH 19:1, then 9:1) to yield [3-(2-methoxyethoxy)phenyl]methanol as an orange oil (3.92 g, 72%).

Provenance & Evidence