Preparation of 3-chloromethyl-4-alkyl-nitrobenzene by chloromethylation

A process for the preparation of a compound of structural formula:

• ##STR11## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, comprising reacting an amide of structural formula:
• ##STR12## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, R.sub.5 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, or phenyl, with phosphorus oxychloride alone or with phosphorus oxychloride in the presence of a solvent methylene chloride, chloroform, ethylene dichloride, benzene, toluene, xylene, chlorobenzene, dimethylformamide or mixtures thereof, at elevated temperatures up to and including the boiling point of the solvent or solvent misture, for a period of time sufficient to essentially complete the reaction, and wherein the amide to phosphorus oxychloride molar ratio is in the range of from 1:1 to 1:4;
• with the condition that when one of the components of the solvent mixture is dimethylformamide, then it is present in the solvent mixture in amounts of one to three molar equivalents per mole of amide.