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

Participants

Reaction Steps

Ethyl 2-(4-((4-hydroxyphenyl)ethynyl)phenoxy)acetate (39.9 mg, 0.135 mmol) was dissolved in THF (1.5 mL) and LiOH.H2O (17.0 mg, 0.405 mmol) in water (1 mL) was added. The mixture was stirred for 2 h. 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 (35.7 mg, 97%) Rf=0.01 (EtOAc:hexanes 1:1 v/v). 1H-NMR (DMSO-d6):□ 4.71 (s, 2H, OCH2); 6.78 (d, 2H, J=8.7 Hz, Ph); 6.93 (d, 2H, J=8.7 Hz, Ph); 7.33 (d, 2H, J=8.1 Hz, Ph); 7.43 (d, 2H, J=8.4 Hz, Ph); 9.87 (s, 1H, OH); 13.00 (s, 1H, COOH). 13C-NMR (DMSO-d6):□ 64.5 (OCH2); 87.2 (CC); 88.6 (CC); 112.8, 114.8, 115.4, 115.7, 132.5, 132.8, 157.6, 157.8 (Ph); 170.0 (COO). MALDI-MS: m/z calculated for C16H12O3 [M]+ 268.0730. found 268.0739.

Provenance & Evidence