Sodium Hydroxide → 2-(1,1'-Biphenyl)-4-YL-2-hydroxypropanoic acid

Participants

Reaction Steps

The crude ethyl 2-[(1,1′-biphenyl)-4-yl]-2-hydroxypropionate was saponified by treating with 100 mL of ethanol and 100 mL of 4.0M NaOH solution. The suspension was stirred for 3 hours, after which a clear solution formed The solution was concentrated, diluted with 150 mL of H2O, washed with 2×50 mL of ether, and acidified to pH 1 with 10% HCl solution. The aqueous phase was extacted with 3×100 mL portions of ether and the combined ether extracts were washed with 50 mL of H2O, 50 mL of brine, dried (MgSO4) and concentrated leaving 18.3 g (72% yield) of racemic 2-[(1,1′-biphenyl)-4-yl]-2-hydroxypropionic acid as a white solid after was recrystallization from CHCl3 and hexanes.

Provenance & Evidence