Hydrochloric Acid → 2-(4-((3-Hydroxyphenyl)ethynyl)phenoxy)ethanoic acid

Participants

Reaction Steps

Ethyl 2-(4-((3-hydroxyphenyl)ethynyl)phenoxy)acetate (48.0 mg, 0.162 mmol) was dissolved in THF (1 mL), and LiOH.H2O (20.4 mg, 0.486 mmol) in water (1 mL) was added. The mixture was stirred over night. and 14% HCl (0.2 mL) was added until pH<1. Water (10 mL) was added, and the mixture was extracted with EtOAc (3×10 mL). The combined EtOAc phases was washed with brine (10 mL), dried over MgSO4, and concentrated under reduced pressure. The product was white/yellow and solid (39.5 mg, 92%). Rf=0.02 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6): □ 4.52 (s, 2H, CH2OH); 7.1 (m, 8H, Ph); 9.71 (s, 1H, OH); 12.94 (s, 1H, COOH). 13C-NMR (DMSO-d6): □ 64.5 (OCH2); 88.2 (CC); 88.7 (CC); 114.7, 114.9, 116.0, 117.6, 122.0, 123.5, 129.8, 132.9, 157.3, 158.0 (Ph); 169.9 (COO). EI-MS: m/z calculated for C16H12O4 [M]+268; [C14H9O2]+209; [C8H8O3]+ 152. found 268, 207, 152.

Provenance & Evidence