Allyl bromide → HCID 54214209, compound

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Reaction Steps

Powdered potassium carbonate (4.14 g) and allyl bromide (3.99 g) were added to a stirred solution of 3-(4-hydroxyphenyl)propanol (4.56 g) in acetone (15 ml) under an atmosphere of argon. The mixture heated at reflux for 20 hours. After cooling to ambient temperature the solid potassium bromide was removed by filtration and washed with ether. The filtrate and washings were combined, washed with 2M aqueous sodium hydroxide (2×20 ml), water (1×20 ml), brine (20 ml), dried (MgSO4) and evaporated. The residue was purified by vacuum flash chromatography on silica gel (Merck 7736) using toluene as eluent to give 3-(4-allyloxyphenyl) propanol as a colourless oil (4.6 g). NMR(CDCl3): 1.3(1H,s), 1.8-2.0(2H,m), 2.6-2.7(2H,t), 3.6-3.7(2H,t), 4.45-4.55(2H,m), 5.2-5.5(2H,m), 5.95-6.15(1H,m), 6.8-6.9(2H,d) and 7.05-7.15(2H,d).

Provenance & Evidence