Process for preparing phenyl esters of substituted acids

Claim 1

A process for preparing a compound of the formula: R--ACH(R.sub.1)CO.sub.2 Ph(CH.sub.2).sub.n --R.sub.2 wherein A is CO 2 (CH(R 1 )CO 2 ) m , S, N(R 4 ) 2 + , P(R 5 ) 2 + or CON(R 6 ); R is C 1 -C 20 alkyl; alkoxylated alkyl, cycloalkyl, aryl or alkylaryl; R 1 is H or CH 3 ; R 2 is SO 3 M, OSO 3 M, CO 2 M, or N+(R 3 ) 3 Q-; n is 0 or an integer from 1 to 4; m is 0 or an integer from 1 to 4; M is H, an alkali metal, an alkaline earth metal, or N(R 3 ) 4 + ; R 3 substituents are independently H or C 1 -C 6 alkyl; R 4 substituents are independently H or C 1 -C 20 alkyl; R 5 substituents are independently C 1 -C 20 alkyl; R 6 is H or C 1 -C 10 alkyl, aryl or alkylaryl; and Q is a halide with the proviso that when A is CO 2 (CH(R )CO 2 ) then R 2 is SO 3 M, OSO 3 M or N+(R 3 ) 3 Q - ; which comprises, in a first step, treating a phenol derivative of the formula: M.sub.1 --OPh(CH.sub.2).sub.n --R.sub.2 with an acid halide of the formula: X--CH(R.sub.1)CO--Y in the optional presence of a solvent and optional presence of a phase transfer catalyst to yield a phenyl ester intermediate of the formula: X--CH(R.sub.1)CO.sub.2 Ph(CH.sub.2).sub.n --R.sub.2 and, in a second step, reacting the intermediate in the optional presence of a solvent with a nucleophile of the formula: RCO 2 (CH(R 1 )CO 2 ) m M 2 , RSM 2 , RN(R 2 ) 2 , RP(R 4 ) 2 or RCON(R 5 )M 2 wherein X and Y are independently Cl or Br; and M 1 and M 2 independently have the same meaning as M.