Benzyl Bromide → 3-Benzyloxy-1-propanol

Participants

Reaction Steps

To a suspension of sodium hydride (5.6 g, 0.14 mole) in tetrahydrofuran (350 ml) is added 1,3-propanediol (15 ml, 0.21 mol). The gummy suspension is stirred at room temperature for 0.5 hour and tetra n-butylammonium iodide (0.54 g) is added followed by benzyl bromide (16.6 ml, 0.14 mole). The mixture is stirred at room temperature for 62 hours. The solvent is evaporated and the residue purified by flash chromatography over silica gel using 1:4 ethylacetate/hexane as eluent to obtain 3-benzyloxypropan-1-ol as a clear oil; 1H NMR (CDCl3): δ7.3 (m, 5H), 4.5 (s,2H), 3.78 (t,8 Hz,2H), 3.65 (t,8 Hz,2H), 1.87 (quintet,8 Hz,2H).

Provenance & Evidence