3,5-Bis-(m-chlorophenyl)4-(2-hydroxyethoxy)benzoic acid ethyl ester → 3,5-Bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid

Participants

Reaction Steps

To a stirred solution of 3,5-bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid ethyl ester (2.009 g, 4.658 mmol) in THF (30 ml) and ethanol (15 ml) was added IN KOH (9.32 ml). After 20 h, the reaction was concentrated in vac. The residue was diluted with water (40 ml) and acidified with 2N HCl (9.32 ml). After 2 h, the solids were collected, rinsed with water, dissolved in EtOAc, dried over Na2SO4, filtered, concentrated in vac, and the residue dried to give the desired product as a white solid (1.708 g, 91%); mp 184-192 (partial melt), solidifies, and melts 200-202° C.; 1H NMR (300 MHz, DMSO-d6) δ 3.12 (q, J=4 Hz, 2H), 3.28 (t, J=4 Hz, 2H), 4.45 (t, J=4 Hz, 1H), 7.45-7.60 (m, 6H), 7.70 (s, 2H), 7.91 (s, 2H), 13.10 (s, 1H).

Provenance & Evidence