Water → 2-(2-Phenylethoxy)ethanol

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (0.93 g, 24.63 mmol) in dry Et2O (60 mL), 2-phenethyloxyacetic acid (1.1 g, 6.15 mmol) in dry Et2O (6 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.93 mL), 3.0 M KOH solution (0.93 mL) and H2O (3.12 mL) were very slowly added. The mixture was stirred at 0° C. for 1 h, filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness. The crude mixture was purified by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:EtOAc (from 100:0 to 60:40) affording the title compound (0.69 g, 68%) as a colorless oil. 1H NMR (DMSO-d6): δ 2.81 (t, J=7.1 Hz, 2H), 3.40-3.44 (m, 2H), 3.45-3.51 (m, 2H), 3.60 (t, J=7.1 Hz, 2H), 4.55 (t, J=5.4 Hz, 1H), 7.15-7.30 (m, 5H).

Provenance & Evidence