3-Hydroxybenzaldehyde → HCID 57940803, compound

Participants

Reaction Steps

A solution of 3-hydroxybenzaldehyde (6.75 g, 55.2 mmol) in DMF (55 mL) was stirred at room temperature under a nitrogen atmosphere as potassium tert-butoxide (6.2 g, 55.3 mmol) was added in portions. The resulting suspension was stirred an additional 15 minutes at room temperature before isopropyl bromoacetate (7.10 mL, 55.2 mmol) was added. The reaction was stirred at room temperature for 15 h and was then quenched with water (250 mL). The resulting aqueous solution was extracted with ethyl acetate, and the combined organic layers were washed several times with water, dried over MgSO4, filtered, and concentrated in vacuo. Purification via medium pressure liquid chromatography (0-10% hexane/ethyl acetate) afforded the title compound (5.2 g, 65%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (d, 6H) 5.04-5.32 (m, 1H) 7.21-7.28 (m, 1H) 7.38 (s, 1H) 7.44-7.60 (m, 2H) 9.98 (s, 1H).

Provenance & Evidence