Sodium Hydroxide → 4-Benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoic acid

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Reaction Steps

Ethyl 4-benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate (2.4 g, 4.5 mmole, example 64) is added to ethanol (50 ml) and 11N sodium hydroxide (4.4 ml, 44 mmole) and refluxed for 8 hours. The solvent is removed in vacuo and the residue is dissolved in dichloromethane with a small amount of water and is acidified to pH6 with 1N HCl. The organic layer is dried over MgSO4 and the solvent removed in vacuo. The crude product is purified by column chromatography (silica, 1% methanol in dichloromethane) to provide the title compound. m.p. 146–149° C.; 1H NMR (300 MHz, CD3OD) d 8.34 (d, 1H), 8.04 (d, 1H), 7.91 (d, 1H), 7.78–7.70 (m, 2H), 7.61 (t, H), 7.37–7.20 (m, 7H), 7.05–6.91 (m, 2H), 6.51 (d, 1H), 6.47 (d, 1H), 5.35 (s, 2H), 5.09 (s, 2H), 5.03 (s, 2H), 2.29 (s, 3H); MS (ESI) 506 (M+H)+.

Provenance & Evidence