Sodium Hydroxide → HCID 18533309, compound

Participants

Reaction Steps

2 N aqueous NaOH (30 mL) was added to ethyl 5-(4-formyl-2,6-dimethylphenoxy)valerate (4.0 g, mw 278.4, 14 mmol; prepared as in Example 18) dissolved in methanol (40 mL) and that 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 (150 mL), washed with ethyl acetate (2×25 mL, discarded), acidified to pH 4 with 6 N aqueous HCl, and extracted with ethyl acetate (3×30 mL). The organic extract was washed with brine (2×75 mL), dried over Na2SO4, filtered and concentrated to yield 3.57 g (99%) of an amber oil. A portion of the oil was purified by flash chromatography on silica (CHCl3-methanol, 45:1) to provide NMR and TLC (Rf origin) pure title product:

Provenance & Evidence