Benzyl Chloride → Benzenamine, 5-chloro-4-nitro-2-(phenylmethoxy)-

Participants

Reaction Conditions

Reaction Steps

In a 500-ml flask, place 18.9 g (0.1 m) of 2-amino-4-chloro-5-nitrophenol (1) and 120 ml of acetone, and heat to 50° C. Add 7.2 g (0.1 m×1.15@90%) of KOH flakes and stir at 55° C. to make a deep red brown solution. Add 6.9 g (0.05 m) of potassium carbonate, 0.8 g of tetrabutyl ammonium bromide and 14.6 g (0.1 m×1.15) of benzyl chloride. Stir the reaction mixture under reflux with fast stirring for 3 hrs. Cool the mixture to room temperature and add 240 ml of water slowly. Stir the resulting slurry and cool to 20° C. Collect solid, wash with water and heptane, and dry in an air oven to give 25.4 g (91%) of 2-benzyloxy-5-chloro-4-nitroaniline (2) as yellow granular solids.

Provenance & Evidence