Water → HCID 21217001, compound

Participants

Reaction Steps

A solution of diethyl 2,3-diphenyl-1,4-benzenedicarboxylate (21.1 g, 46.0 mmol) in anhydrous THF (175 mL) was added dropwise with stirring over a 0.5 hour period to a suspension of lithium aluminum hydride (7.89 g, 208 mmol) in 350 mL of anhydrous THF at 0° C. This solution was stirred at room temperature for 1 hour and refluxed for 24 hours. The solution was then cooled and treated with: 1) 8 mL of water, added dropwise and stirred carefully for 0.25 hour, 2) 24 mL of 15% NaOH with stirring for an additional 0.25 h, and 3) 24 mL of water with additional stirring for 0.25 hour. The THF was evaporated and the resulting mixture was stirred for 12 hours with a 10% (v/v) H2SO4 solution. The product was filtered and recrystallized from aqueous ethanol to give a white solid (12.6 g, 73% yield): mp 136-7° C.

Provenance & Evidence