4-Chlorophenol → Methyl 4-(p-chlorophenoxy)butyrate

Participants

Reaction Steps

A mixture of methyl 4-bromobutyrate (1.5 g, 8.29 mmol), 4-chlorophenol (1.17 g, 9.11 mmol), potassium carbonate (2.86 g, 20.7 mmol), and anhydrous N,N-dimethylformamide (5 mL) was added to a 25 mL RBF with a magnetic stirring bar. The mixture was allowed to stir at room temperature for 16 hours. Progress of the reaction was monitored by analytical HPLC with UV detection (Rt=6.5 min). The mixture was added to stirring ice/water (150 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated aqueous NaCl (2×30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using a gradient elution of 0-100% ethyl acetate in hexanes to afford the title compound as a clear oil (1.45 g, 76% yield).

Provenance & Evidence