3-(3'-Hydroxyphenyl)propionic acid → HCID 57672487, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3-hydroxyphenyl)-propionic acid (0.031 g, 0.186 mmol) (commercially available from Alfa, CAS No. 621-54-5) in THF (1 mL) was added tetrabutylphosphonium hydroxide (40 wt % solution in water) (0.27 g, 0.39 mmol). The mixture was then cooled in an ice bath to 0° C. After 10 minutes, 13.5 (0.055 g, 0.191 mmol) was added at 0° C. Upon complete addition, the reaction was allowed to warm to room temperature. After 44 hours, the solvent was removed under vacuum. The residue was diluted with water and acidified with 2M HCl to pH 2. The mixture was extracted with EtOAc. The layers were separated and the solvent was removed under vacuum to yield an oil that was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 65% EtOAc in hexanes) to yield a colorless film 13 (0.023 g, 28% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 7.39 (1H, dd, J=8.0, 1.8 Hz), 7.31 (1H, d, J=2.0 Hz), 7.23 (1H, t, J=8.0 Hz), 7.10 (1H, m), 6.99 (1H, d, J=7.8 Hz), 6.90 (5H, m), 5.04 (2H, s), 3.82 (3H, s), 2.95 (2H, t, J=7.8 Hz), 2.72 (2H, m), 1.85 (1H, m), 0.87 (2H, m), 0.68 (2H, m).

Provenance & Evidence