Ethanol → 5-Phenylpent-4-enyl-1-ol

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Into a flask fitted with dropping funnel, mechanical stirrer and reflux condenser with nitrogen inlet was introduced 2 ml of dry xylene (a) and 69 g (3.0 g-atom) of sodium (b). The xylene was heated until the metal softened, the heating mantel removed, the flask briskly shaken to divide the sodium into sand-like particles and the flask allowed to cool. The xylene was removed and the sodium sand washed with dry ether (3×100 ml) and the finely divided metal residue covered with 1.2 liters of dry ether (c). To the rapidly stirred suspension was added 256 g (1.3 mole) of 3-chloro-2-phenyltetrahydropyran (e) in 20 ml of ether (f). The addition was dropwise until the reaction began, as evidenced by a blue color and the remainder of the halide was added over 90 minutes. The resulting gray slurry was stirred, refluxed after one hour of addition, with the color changing to cream color and the reaction vessel then cooled in an ice bath and with rapid stirred 40 ml of ethanol followed by 9 ml of water were added cautiously. After separation of the layers, the aqueous phase was extracted with ether (3×200 ml), the combined ethereal fractions washed with brine (200 ml) and dried over potassium carbonate. In vacuo removal of solvent left 219 g of a red liquid which was fractionally distilled and the fraction boiling at 94°-95°/0.18 mm Hg collected providing 61.5 g (29% yield).

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