Benzyl Alcohol → 5-benzyloxy-N-methyl-2-nitroaniline

Participants

Reaction Conditions

Reaction Steps

Benzyl alcohol (49.6 mL, 0.48 mol), tetrabutyl ammonium chloride (6.66 g, 24.0 mmol) and potassium carbonate (40.0 g, 0.29 mol) were added to a toluene solution (200 mL) of 5-fluoro-N-methyl-2-nitroaniline (40.8 g, 0.24 mol), and the mixture was heated under reflux for 3.5 hours. The reaction solution was cooled, and 100 mL of water was added thereto. Thereafter, the mixture was stirred for 1 hour at 60 to 70° C. After the mixture was stirred under ice cooling for 30 minutes, precipitated crystals were collected by filtration. The resulting crystals were washed with water, and dried at 50° C., thereby obtaining 57.1 g of an orange, powdery target compound (yield: 92%).

Provenance & Evidence