Hydrochloric Acid → 3-Benzyloxy-1-propanol

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Reaction Steps

In a 2 L flask, a solution of 1,3-propane-diol (3) (38 g, 0.5 moles) and benzyl bromide (85.5 g, 0.5 moles) in dry tetrahydrofuran (500 mL) is cooled to 0° C. (internal temperature) using ice/salt mixture. Potassium-t-butoxide (56 g, 0.5 moles) is added in portions, maintaining the temperature below +20° C. The mixture is stirred at room temperature overnight, then poured into 2N HCl (1 L) and water (1 L). After saturating with NaCl, the mixture is extracted with ether (1.5 L). The organic phase is washed with water (3×), dried (Na2SO4) and evaporated to give an oil (81 g). This is distilled (oil pump) to give pure 14 as a colourless liquid: 58.5 g (70%), bp about 0.05 95°-105° C.

Provenance & Evidence