Process for the in-solvent, in-situ generation of haloalkyl alkyl ethers useful to produce N-substituted-2-haloacetanilides

A process for preparing a compound of the formula ##STR31## where X.sub.1 is chloro, bromo or iodo;

• R is C.sub.1-10 alkyl, C.sub.3-10 alkenyl, C.sub.3-10 cycloalkyl, C.sub.3-10 alkynyl, C.sub.1-5 alkoxy (C.sub.2-5) alkyl, mono-halo (C.sub.2-5) alkyl, mono-halo (C.sub.3-5) alkenyl or ##STR32## y is the integer 2, 3 or 4;
• with the proviso that when R is alkenyl or alkynyl the carbon atom attached to the oxygen may not share a double or triple bond with an adjacient carbon atom;
• R.sub.2 is C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.3-8 alkynyl, C.sub.1-8 alkoxy, C.sub.1-8 alkoxy (C.sub.1-5) alkyl, halo (C.sub.1-5) alkyl, halogen, NO.sub.2, C.sub.1-5 alkoxy (C.sub.1-5) alkoxy or C.sub.1-5 alkoxy (C.sub.1-5) alkoxy (C.sub.1-5) alkoxy;
• R.sub.3 is hydrogen, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.1-8 alkoxy, C.sub.1-8 alkoxy (C.sub.1-5) alkyl, halo (C.sub.1-5) alkyl, halogen or NO.sub.2 ;
• R.sub.4 is C.sub.1-8 alkyl, halo (C.sub.1-5) alkyl, halogen or NO.sub.2 ;
• n is the integer zero, one or two;
• which comprises reacting, in a solvent and in the presence of a phase transfer catalyst, an alcohol of the formula
• ROH (V)
• (where R is as defined in Formula IV);
• formaldehyde, an acid halide and a compound of the formula ##STR33## (where X.sub.1, R.sub.1, R.sub.3, R.sub.4 and n are as defined in Formula IV);
• followed by addition of excess base.