Benzyl Bromide → cis-4-Benzyloxy-2-buten-1-ol

Participants

Reaction Steps

Benzyl bromide (8.0 g, 47 mmol) was added over a period of 30 minutes to a mixture of but-2-ene-1,4-diol (25.0 g, 281 mmol) and sodium hydride (2.2 g, 94 mmol) in DMF (100 mL) at 0° C. The mixture was stirred for 16 hours at room temperature. The mixture was then diluted with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (methanol/ethyl acetate) to afford (2Z)-4-(benzyloxy)but-2-en-1-ol. 1H NMR (400 MHz, CD3OD) δ 7.34-7.27 (m, 5H), 5.75-5.64 (m, 2H), 4.50 (s, 2H), 4.12-4.09 (m, 4H).

Provenance & Evidence