Benzyl Bromide → 5-(Benzyloxy)pentan-1-ol

Participants

Reaction Steps

1,5-pentanediol (2.10 mL, 20.0 mmol, 1.0 equiv.) was dissolved in CH2Cl2 (100 mL). Ag2O (6.95 g, 30.0 mmol, 1.5 equiv.) and benzyl bromide (2.62 mL, 22.0 mmol, 1.1 equiv.) were added to the solution sequentially. The flask was wrapped with aluminium foil, and the solution was stirred at room temperature for 18 h. The solution was filtered through a pad of celite, eluting with CH2Cl2, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, Ethyl Acetate (EtOAc): petroleum ether (pet ether)=3:17 to 1:1) to give the alcohol as a colorless oil. 1H NMR (500 MHz, CDCl3) δ=7.37-7.26 (m, 5H), 4.50 (s, 2H), 3.64 (t, J=6.5 Hz, 2H), 3.49 (t, J=6.5 Hz, 2H), 1.70-1.63 (m, 2H), 1.62-1.55 (m, 2H), 1.50-1.42 (m, 2H), 1.34 (br s, 1H) ppm; 13C NMR (125 MHz, CDCl3) δ=138.8, 128.6, 127.8, 127.7, 73.2, 70.5, 63.1, 32.8, 29.7, 22.7 ppm; Low Resolution Mass Spectrometry (LRMS) (ESI+ve) m/z: 217 (M+Na+).

Provenance & Evidence