Sodium Hydroxide → HCID 11075482, compound

Participants

Reaction Steps

2 N aqueous NaOH (10 mL) was added to ethyl 5-(4-formyl-3-hydroxyphenoxy)valerate (1.5 g, mw 266.3, 5.8 mmol; prepared as in Example 16) dissolved in methanol (20 mL) and the solution stirred at 25° C. for 1 hour, at which point TLC (CHCl3-methanol, 99:1) indicated the reaction was complete. Methanol was removed under reduced pressure and the reaction diluted with water (50 mL), washed with ethyl acetate (3×15 mL, discarded), acidified to pH 4 with 6 N aqueous HCl, and extracted with ethyl acetate (4×25 mL). The combined organic extracts were washed with brine (2×50 mL), dried over Na2SO4, filtered, and concentrated to yield 1.35 g (98%) of a white solid. A portion of the solid was purified by flash chromatography on silica (CHCl3-methanol, 45:1) and recrystallized from boiling ethyl acetate-hexane to provide NMR and TLC (Rf origin) pure title product; 1H NMR (500 MHz, CDCl3, 294 K) δ11.47 (s), 9.71 (s), 7.42 (d, J=8.6; 1H), 6.53 (dd, J=2.3, 8.6; 1H), 6.41 (d, J=2.3; 1H), 4.04 (t, J=5.8; 2H), 2.46 (t, J=7.0; 2H), 1.86 (m; 4H).

Provenance & Evidence