Hydrochloric Acid → beta-(Hydroxymethyl)-beta-phenylpropionitrile

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Reaction Steps

β-(Carbomethoxy)-β-phenylpropionitrile (144 g, 0.76 mol) is dissolved in dimethoxyethane (1500 mL) and NaBH4 (63.5 g, 1.67 mol) is cautiously added. The reaction mixture is stirred for 30 minutes and then heated at reflux for 2 hours. After this time the resulting solution is allowed to cool to ambient temperature and is poured onto ice. The mixture is then treated with 2N HCl (1500 mL) and is subsequently diluted with Et2O (1500 mL). The organic phase is washed with H2O (1×1000 mL), saturated NaCl solution (2×1000 mL), dried over MgSO4 and concentrated in vacuo to yield β-(hydroxymethyl)-β-phenylpropionitrile.

Provenance & Evidence