Hydrochloric Acid → 4-[(1-{4-[(4-Butylphenyl)ethynyl]phenyl}pentyl)oxy]-2-hydroxybenzoic acid

Participants

Reaction Steps

To a solution of 7-[(1-{4-[(4-butylphenyl)ethynyl]phenyl}pentyl)oxy]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (370 mg, 0.74 mmol) in EtOH (10 mL) was added an aqueous solution of NaOH (0.75 mL, 3.75 mmol, 5N) and the resulting mixture was stirred overnight at rt. An aqueous solution of HCl (10 mL, 1N) was added and the resulting reaction mixture was extracted with Et2O (3×). The combined organic layers were washed with water and brine, dried over MgSO4 and the solvents were removed under reduced pressure to give 320 mg (94%) of the title compound as a colorless oil. HPLC, Rt: 6.8 min (purity: 99.8%). LC/MS, M−(ESI): 455.3. 1H NMR (CDCl3) δ:10.5 (s, 1H); 9.66 (brs, 1H), 7.72 (d, J=9.0 Hz, 1H), 7.48 (d, J=8.3 Hz, 2H), 7.41 (d, J=8.3 Hz, 2H), 7.28 (d, J=8.3 Hz, 2H), 7.15 (d, J=8.3 Hz, 2H), 6.45 (dd, J=2.3 Hz, J=9.0 Hz, 1H), 6.35 (d, J=2.3 Hz, 1H), 5.14 (t, J=7.8 Hz, 1H), 2.61 (t, J=7.9 Hz, 2H), 2.09-1.93 (m, 1H), 1.90-1.75 (m, 1H), 1.66-1.75 (m, 1H), 1.66-1.19 (m, 8H), 0.96-0.84 (m, 6H).

Provenance & Evidence