Hydrochloric Acid → 2-(4-((4-(Hydroxymethyl)phenyl)ethynyl)phenoxy)ethanoic acid

Participants

Reaction Steps

Ethyl 2-(4-((4-(hydroxymethyl)phenyl)ethynyl)phenoxy)acetate (54.0 mg, 0.174 mmol) was dissolved in THF (1 mL), and LiOH.H2O (10.9 mg, 0.261 mmol) in water (0.5 mL) was added. The mixture was stirred for 1.5 h. and 3% HCl (0.5 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 (48.0 mg, 98%). Rf=0.04 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6): □ 4.52 (s, 2H, CH2OH); 4.73 (s, 2H, OCH2); 5.26 (s, 1H, CH2OH); 6.95 (d, 2H, J=8.7 Hz, Ph); 7.35 (d, 2H, J=7.8 Hz, Ph); 7.48 (m, 4H, Ph); 12.99 (s, 1H, COOH). 13C-NMR (DMSO-d6): □ 62.0 (CH2OH); 64.0 (OCH2); 87.7 (CC); 88.3 (CC); 114.3, 114.4, 120.3, 126.1, 130.5, 132.3, 142.6, 157.5 (Ph); 169.4 (COO). EI-MS: m/z calculated for C17H14O4 [M]+ 282; [C15H11O2]+ 223; [C8H8O3]+ 152. found 282, 223, 152.

Provenance & Evidence