Ethanol → HCID 22996179, compound

Participants

Reaction Steps

To a solution of 5-chloromethyl-2-methoxy-benzonitrile (254 mg, 1.399 mmol) in ethanol (10 mL) was added potassium carbonate (387 mg, 2.798 mmol). The mixture was heated at reflux for 12 h. Upon cooling to room temperature, the solvent was removed. Water (2-5 mL) was added and the product was extracted with diethyl ether (2×20 mL). The organic layers were washed with brine (1×5 mL) and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 20% ethyl acetate in hexanes yielded 5-ethoxymethyl-2-methoxy-benzonitrile (182 mg, 68%).

Provenance & Evidence