Hydroxyphenylacetic acid → 3,3,3-Triphenylpropyl 2-(4-hydroxyphenyl)acetate

Participants

Reaction Steps

To triphenylpropanol (3.98 mmol), 4-hydroxyphenylacetic acid (3.98 mmol), and triphenylphosphine (4.39 mmol) in dry THF (20 mL) at 0° C. under a nitrogen atmosphere, was added DEAD (4.39 mmol) in dry THF (20 mL) over 15 minutes. The reaction was stirred at room temperature for 16h and then the THF was evaporated. The residue was chromatographed on silica gel using 15-30% EtOAc/hexanes. White solid, mp=136°-138° C. (ether), 34% yield. 1H NMR δ 7.15-7.27 (m, 15H), 7.10 (d, J=8.5 Hz, 2H), 6.77 (d, J=8.5 Hz, 2H), 4.90 (s, 1H), 3.90 (t, J=7.9 Hz, 2H), 3.47 (s, 2H), 2.93 (t, J=7.9 Hz, 2H). Anal. calcd. for C29H26O3 : C, 82.44; H, 6.20. Found: C, 82.29; H, 6.24.

Provenance & Evidence