Allyl bromide → Ethylene glycol diallyl ether

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Reaction Steps

Sodium hydride (NaH, 5.0 g, 0.208 mol) was slowly added to a solution of 2-allyloxy-ethanol (20 mL, 0.187 mol) while stirring. Allyl bromide (32 mL, 0.370 mol) was added and the mixture was stirred at 60° C. for 10 hours. After cooling, the reaction mixture was filtered and a dark oil was obtained after solvent evaporation. The oil was fractionally distilled to give 22 grams of 3-(2-allyloxy-ethoxy)-propene (0.155 mol, yield 83%) as a colorless oil. 1H NMR (400 Mz, CDCl3): δ 3.6 (t, 2H), 4.0 (d, 2H), 5.1 (d 1H), 5.3 (d 1H), 5.9 (q, 1H).

Provenance & Evidence