4-Nitrotoluene → HCID 13115425, compound

Participants

Reaction Steps

A solution of p-nitrotoluene (6.85 g; 0.05 mol) in concentrated sulfuric acid (60 ml) is cooled in an ice bath and N-(hydroxymethyl)acetamide (4.45 g; 0.05 mol) is added. The reaction mixture is stirred until a solution is obtained and then continuously stirred for 16 hours at 55° C. The mixture is then poured onto ice and the resulting precipitate is isolated. This solid material is extracted with 85 ml of butyl acetate on a steambath. Concentration of the butyl acetate solution with subsequent cooling gives 3.9 g (i.e., 38% yield) of product. The butyl acetate insoluble material (2.5 g) is methylene bis(4-nitro-o-toluene).

Provenance & Evidence