Resorcinol → 6-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carboxylic acid

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Reaction Conditions

Reaction Steps

To a round bottom flask, add 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde (3.0 g, 4.34 mmol), resorcinol (531 mg, 4.8 mmol), THF (8 mL), ethanol (8 mL) and acetic acid (0.9 mL). Stir the mixture at 25° C. for 5 min. Add slowly sodium chlorite (1.3 g, 11.2 mmol) in water (8 mL) to the reaction mixture. Stir the mixture at 80° C. for 2 hours. Quench the reaction mixture with ice-water. Add ethyl acetate to the vessel with stirring. Wash the mixture with dilute NaOH three times and discard the organic phase. To the aqueous layer, add water so the pH was adjusted to 5-6. Extract the aqueous layer with ethyl acetate five times and discard the aqueous phase. Dry the organic layer over MgSO4, filter, and concentrate to dryness, which was further purified to give 400 mg of 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carboxylic acid. 1HNMR (d-DMSO, 300 MHZ): 9.97 (1H, s) 7.12 (1H, m), 6.86 (5H, m), 6.71 (1H, m), 4.27 (2H, m), 3.73 (3H, s), 4.26 (2H, s), 3.41 (3H, m), 2.82 (2H, m), 2.59 (2H, m), 1.70 (6H, m).

Provenance & Evidence