Tetrahydrofuran → 2-(3-(Benzyloxy)phenyl)-2-methylpropanal

Participants

Reaction Steps

To a 15° C. solution of 325 g. (1.25 mole of 2-(3-benzyloxyphenyl)-2-methylpropionitrile in 1.85 liters of tetrahydrofuran was added 1.6 moles of diisobutylaluminum hydride as a 1.3 M solution in hexane (reaction temperature is maintained at 15°-18° C.). The reaction mixture was allowed to warm to room temperature and was stirred 2 hours longer. It was then quenched by addition to a solution of 170 ml. of concentrated sulfuric acid in 670 ml. of water (temperature ≤30° C.). The resultant mixture was allowed to warm to room temperature and was then stirred an additional 2 hours. The organic layer was separated and the aqueous phase extracted once with one liter of ether. The combined organic phase was washed with 500 ml. of water and 500 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to yield 315 g. (99%) of the title product.

Provenance & Evidence