Phenol → Allyl phenyl ether

Participants

Reaction Conditions

Reaction Steps

To a round-bottomed flask containing a solution of phenol (30 g, 319 mmol) in acetonitrile (150 ml) at room temperature was added potassium carbonate (66 g, 478 mmol) and allyl bromide (49.8 g, 412 mmol). The mixture was heated to 50° C. and stirred for 3.5 hours. The solids were filtered out and the filtrate was concentrated to a minimum volume. The crude material was diluted with water (200 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (2×100 ml), dried over anhydrous magnesium sulfate, filtered, and concentrated to afford crude allyloxybenzene as brown oil (35 g); 1H NMR (300 MHz, CDCl3): δ 7.20-7.30 (m, 2H), 6.89-6.96 (m, 3H), 5.99-6.12 (m, 1H), 5.41 (d, J=17.1 Hz, 1H), 5.28 (d, J=10.5 Hz, 1H), 4.52 (d, J=5.1 Hz, 2H).

Provenance & Evidence