(4-Hydroxyphenoxy)acetic acid → 4-(2-Hydroxyethoxy)phenol

Participants

Reaction Steps

To a solution of 4-hydroxyphenoxyacetic acid (4.9 g, 29 mmol) (Aldrich) in anhydrous tetrahydrofuran (30 mL) at 0° C. was added borane tetrahydrofuran (1 M, 90 mL, 90 mmol) dropwise. The reaction mixture was then stirred at room temperature for 2 h. The mixture was concentrated and residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over MgSO4, and concentrated to give title compound as a yellow oil (4.2 g, 94%)

Provenance & Evidence