Process for the preparation of 2,6-dialkyl-N-alkoxymethyl-2-chloro-acetanilides

In a process for the preparation of a 2',6'-dialkyl-N-alkoxymethyl-2-chloro-acetanilide compound of the general formula (I), ##STR9## wherein R.sub.1, R.sub.2 and R.sub.3 are identical or different and stand for straight-chained or branched C.sub.1-4 alkyl groups, by converting a dialkyl aniline into a Schiff base, and reacting the resulting Schiff base with a haloacyl halide and an alkanol, and in which a dialkyl aniline of the general formula (II), ##STR10## wherein R.sub.1 and R.sub.2 are as defined above, is treated with aqueous formaldehyde solution in an apolar solvent at a temperature of 30.degree. to 80.degree. C.;

• the improvement in which the solution of the resulting oxymethyl derivative of the general formula (IIIA), ##STR11## wherein R.sub.1 and R.sub.2 are as defined above, formed with said apolar solvent is separated from the aqueous formaldehyde solution at an elevated temperature and then the separated apolar solvent containing the oxymethyl derivative of the general formula (IIIA) is dehydrated by azeotropic distillation at a temperature above 90.degree. C. to remove the last traces of water, the azomethine derivative of the general formula (III), ##STR12## wherein R.sub.1 and R.sub.2 are as defined above, obtained in the dehydration step is reacted with chloroacetyl chloride in the same apolar solvent medium, the resulting chloromethyl derivative of the general formula (IV), ##STR13## wherein R.sub.1 and R.sub.2 are as defined above, is reacted with an alcohol of the general formula (V),
• R.sub.3 -OH (V)
• wherein
• R.sub.3 is as defined above, in an amount sufficient to bind the hydrochloric acid liberated in the reaction, the reaction mixture is admixed with water, and the organic phase containing the required end-product is separated.