Water → (2,3-Bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol

Participants

Reaction Steps

To a solution of methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate (2.0 g, 7.03 mmol) in dry THF (10 mL) was added dropwise a 1M solution of lithium aluminum hydride in THF (7.0 mL), and the resulting mixture was stirred at rt for 1 h. Then, water (0.27 mL) was added slowly, followed by 15% aqueous sodium hydroxide (0.27 mL), and more water (0.81 mL). The mixture was filtered, the filter cake washed with ethyl acetate, and the combined filtrate was concentrated. Column chromatography on silica (1:1 hexanes/ethyl acetate) gave (2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (1.13 g, 63% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ6.96 (dd, 1H), 6.86 (m, 2H), 4.60 (d, 1H), 4.33 (m, 2H), 4.24 (t, 1H), 4.13 (m, 2H), 3.75 (m, 2H), 3.70 (m, 2H), 3.43 (s, 6H).

Provenance & Evidence