Lithium hydroxide, monohydrate → 4-{[4-(4-Butyl-phenylethynyl)-benzyl]-hexyl-amino}-2-hydroxy-benzoic acid

Participants

Reaction Steps

To a solution of 7-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (613 mg, 1.2 mmol) in THF (18 mL) was added a suspension of lithium hydroxide monohydrate (1.47 g, 35.1 mmol) in water (5.0 mL). The resulting mixture was refluxed for 48 hrs. The reaction mixture was diluted with Et2O (60 mL) and washed with an aqueous solution of HCl (3×15 mL, 1N) and brine. The organic layer was dried over MgSO4 and the solvents were removed under reduced pressure to give 443 mg (78%) of the title compound as a yellow powder. HPLC, Rt: 6.2 min (purity: 97.7%). LC/MS, M−(ESI): 482.2. 1H NMR (CDCl3) δ: 10.59 (s, 1H), 7.66 (d, J=9 Hz, 1H), 7.45 (m, 4H), 7.13 (m, 4H), 6.21 (m, 1H), 6.14 (m, 1H), 4.58 (s, 2H), 3.40 (m, 2H), 2.60 (t, J=7.5 Hz, 2H), 1.72-1.51 (m, 2H), 1.42-1.20 (m, 10H), 0.95-0.82 (m, 6H).

Provenance & Evidence