Water → 4-(4-(3,5-Bis(4-(4-carboxyphenyl)phenyl)phenyl)phenyl)benzoic acid

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Reaction Steps

Trimethyl 4,4′,4″-(benzene-1,3,5-triyl-tris(benzene-4,1-diyl))tribenzoate (2.00 g, 2.82 mmol), 2.2 g of NaOH, THF, water, and methanol (200, 80, and 50 mL, respectively) were mixed in a 1 L round bottom flask equipped with a magnetic stirring bar, and the mixture was stirred for 2 days at room temperature. The solution was evaporated under vacuum. The residue was acidified with 3 M HCl. The white solid was collected by filtration, washed with methylene chloride and methanol and dried in vacuum overnight (1.80 g, 96%): mp 326° C.; 1H-NMR (DMSO-d6, 400 MHz) δ 13.07 (br, 3H) 8.07 (d, 6H, J=8.0 Hz), 8.06 (s, 3H), 8.05 (d, 6H, J=8.0 Hz), 7.91 (d, 6H, J=7.6 Hz), 7.89 (d, 6H, J=7.2 Hz); 13C-NMR (DMSO-d6, 100 MHz) δ 168.0, 144.6, 141.9, 140.7, 139.2, 130.9, 130.6, 128.8, 128.4, 127.6, 125.3; FT-IR (KBr, 4000-400 cm−1) 3448 (br), 3029 (br), 2661 (w), 2536 (w), 1925 (w), 1686 (s), 1606 (s), 1419 (m), 1276 (m), 1177 (m), 1118 (m), 1003 (m), 824 (s), 773 (s); MALDI-TOF MS (m/z) [M]+ 666.2976 (found), 666.2042 (calcd. for C45H30O6).

Provenance & Evidence