5-(Benzyloxy)-1,3-dimethyl-2-nitrobenzene → 4-Benzyloxy-2,6-dimethylaniline

Participants

Reaction Steps

Zinc dust is added to a solution of 5-benzyloxy-2-nitro-m-xylene (22.9 g) in 250 ml of glacial acetic acid. The reaction mixture is stirred until the solution is colorless. The reaction mixture is cooled, filtered through celite to remove excess zinc and the filtrate diluted with H2O and cooled with ice. NH3 is added to make the solution slightly alkaline followed by a small amount of sodium hydrosulfite. The product is filtered, dissolved in methylene chloride, dried and concentrated to give 18.3 grams of a tan solid.

Provenance & Evidence