Preparation of aryl carbonyl compounds

A process for the preparation of an aromatic carbonyl compound having the formula

• (R).sub.s ArDCOY, (R).sub.s ArDCOBD(R').sub.t, (R).sub.s ArDCOBDArD(R).sub.s, (R).sub.s ArDCODAr(R).sub.s, or (R).sub.t DBCOArDCOBD(R').sub.t
• wherein each s and t are independently 1,2, or 3 and each R, Ar, B, D and R, are independently as defined below, which process comprises reacting a first reactant, consisting of a substituted or unsubstituted aromatic compound containing at least one activated hydrogen atom of the formula
• (R).sub.s ArDH
• wherein Ar is a homo or hetero-aromatic mono, di, or tri-cyclic moiety or a fused homo-aromatic condensed system containing less than 20 aromatic carbon atoms, or a hetero-aromatic system containing less than 8 nitrogen atoms, each R is as defined below and D is
• --(ZAr).sub.n --(ZAr).sub.m --(ZAr).sub.p --
• wherein n, m, and p are each independently 0,1,2 or 3, provided that n+m+p is less than 4, and z is --CO--, --SO.sub.2 --, --CO--C.sub.6 H.sub.4 --CO--, --O--(CF.sub.2).sub.q --O-- or V, provided that when n+m+p>0, any Ar group which contains an activated hydrogen atom is also linked to a V group, where V is a divalent radical of the formula
• --O--, --S--, --N=N--, --(CF.sub.2).sub.q --, --(CH.sub.2).sub.q --, or --C(CH.sub.3).sub.2
• wherein q is 1 to 20;
• with a second reactant, consisting of phosgene, or a mono-, di- or polyfunctional organic carboxylic acid, acid halide, alkyl ester, or anhydride, or a monofunctional acyl compound of the general formula
• YCOBD(R').sub.t or O(COBD(R').sub.t).sub.2
• where t is 1, 2, or 3, or a difunctional acyl compound of the general formula
• YCOBDCOY
• wherein each B is independently a divalent substituted or unsubstituted aliphatic or cycloaliphatic group or Ar, and R and R' which may be the same or different are a H, Br, Cl, or F atom or hydroxy, alkoxy, alkyl, aralkyl, unsubstituted or mono- or disubstituted amino, nitro, ester, acid, amide or imide group, and each Y represents a Br, Cl, or F atom or a hydroxy or alkoxy group, subject to the proviso that any aromatic ring which contains an activated hydrogen atom also contains less than 2 alkoxy groups and to the further proviso that the aromatic carbonyl compound contains less than 2 identical directly linked sequences containing at least one --SO.sub.2 -- or --CO-- in a reaction medium comprising:
• (A) A Lewis acid in an amount of about one equivalent per equivalent of carbonyl groups or other basic species present in the reactant system plus about one equivalent per equivalent of controlling agent, plus an amount effective to act as a catalyst for the reaction;
• (B) a controlling agent, in an amount from 0.1 to 4 equivalents per equivalent of acid halide groups present in the reactant system, comprising:
• (i) R(OX).sub.a which must be present in the reaction medium together with the Lewis acid before any reactant containing acid halide groups is added,
• (ii) R(COOX).sub.a, or
• (iii) (RO).sub.b Y, which, if the Y--O linkage(s) are reactive to acid halide groups, must be present in the reaction medium together with the Lewis acid before any reactant containing acid halide groups is added,
• where R is a monovalent or polyvalent organic group compatible with the reactant(s) and the other components of the reaction medium,
• each X independently is a hydrogen atom or a monovalent metal atom,
• each a independently is 1 or 2,
• Y is a multivalent metal atom, and
• b is an integer equal to the valency of Y;
• and
• (C) a non-protic diluent is an amount from 0 to about 93% by weight, based on the weight of the total reaction mixture.