Sulfuric Acid → 5-(4-Fluorophenoxy)-1-penten-4-ol

Participants

Reaction Steps

Allyl bromide (~0.5 g.) is added to a stirred suspension of magnesium turnings (4.49 g., 0.185 mole) in dry ether (50 ml.) at 25° C. Upon initiation of reflux, the reaction suspension is stirred and treated with a solution of allyl bromide (24.2 g., 0.2 mole) and 4-fluorophenoxyacetaldehyde (19 g., 0.123 mole) in dry ether (110 ml.) added at such a rate as to maintain a gentle reflux. The resulting reaction mixture is heated at reflux for 1 hour, cooled to 0°-5° C., and treated with 3.2 N sulfuric acid (70 ml.), providing a heterogeneous mixture. After separating the phases, the aqueous phase is extracted with ether three times. The organic phase is combined with the ethereal extracts and washed with 5% aqueous sodium bicarbonate, dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo affords an oily residue which is distilled to provide the title compound as a colorless oil (18.6 g., 77%), bp0.03 73° C.; pmr (CCl4) δ2.32 (2H, t), 2.54 (H, m) 3.6-4.1 (3H, m), 4.8-5.05 (H, m) 5.05-5.25 (H, m), 5.4-6.3 (H, m) and 6.6-7.1 (4H, m).

Provenance & Evidence