Dichloromethane → 2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-6-trifluoromethyl-benzoic acid

Participants

Reaction Steps

A solution of 2-[3-(quinolin-2-ylmethoxy)-benzyloxy]-6-trifluoromethyl-benzaldehyde (46 mg, 0.1 mmol, example 50) in 2-methyl-2-butene (1 mL), t-butanol (2 mL) and water (2 mL) is treated with sodium dihydrogenphosphate dihydrate (153 mg, 1.1 mmol) and sodium chlorite (198 mg, 2.2 mmol). After 45 min. the reaction is partioned between dichloromethane (50 mL) and water (50 mL). The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo to provide the title compound: m.p. 184–185° C.; 1H NMR (300 MHz, CDCl3) δ 8.28 (d, 1H), 8.12 (d, 1H), 7.82–7.75 (m, 2H), 7.66–7.55 (m, 2H), 7.42 (dd, 1H), 7.30–7.27 (m, 2H), 7.16 (d, 1H), 7.07 (dd, 1H), 6.88 (d, 1H), 6.77 (dd, 1H), 5.44 (s, 2H), 5.07 (s, 2H); MS (ESI) 454 (M+H)+.

Provenance & Evidence