Citric Acid → 1-Chloro-2-methoxy-4-methylbenzene

Participants

Reaction Steps

Sodium hydride (60% dispersion, 3.0 g, 77 mmol) was added in three portions to a solution of 2-chloro-5-methylphenol (10.0 g, 70.1 mmol) in DMF (100 mL) at 0° C. under nitrogen. Methyl iodide (5.0 mL, 77 mmol) was added and the solution was warmed to RT. After 1 h, 10% aqueous citric acid (200 mL) and EtOAc (1.0 L) were added. The layers were separated and the aqueuos layer was extracted with EtOAc. The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and evaporated. Purification was accomplished by column chromatography (hexane/EtOAc) to afford the title compound (12 g, 100%).

Provenance & Evidence