Diethyl Ether → 2-(4-Bromophenethyl)-benzyl alcohol

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Reaction Steps

Lithium aluminum hydride, 3.8 g. (0.1 mole), is wegihed under nitrogen, transferred to a dry, nitrogen-flushed reaction flask, and suspended in 300 ml. of absolute ether. The mixture is stirred at reflux for 30 minutes and then, after cooling to room temperature, a solution of 36.16 g. (0.108 mole) of ethyl 2-(4-bromophenethyl)-benzoate in 100 ml. of absolute ether is added dropwise. The mixture is stirred at room temperature overnight. The excess lithium aluminum hydride is decomposed by the addition of 5 ml. of ethyl acetate and the mixture then is hydrolyzed by the addition of 30 ml. of saturated ammonium chloride solution. The ethereal layer is separated and the aqueous layer re-extracted with ether. Evaporation of the combined, washed, and dried ethereal extracts under reduced pressure leaves the product as the residual solid, m.p. 72°-75.5° C. Recrystallization from hexane-cyclohexane affords purified material, m.p. 74°-75.5° C. A sample for analysis melts at 75°-76.5° C. after recrystallization from hexane.

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