Friedel-crafts preparation of aromatic ketones with an inoganic salt controlling agent

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

• (R).sub.s ArDCOBD(R').sub.t, (R).sub.s ArDCOBDCOArD(R).sub.s, (R).sub.s ArDCODAr(R).sub.s, or (R').sub.t DBCOArDCOBD(R').sub.t
• wherein each s and t is independently 1, 2 or 3 and each R, Ar, B, D and R' is independently as defined below,
• which 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 tricyclic moiety or a fused homo-aromatic condensed system containing less than 20 aromatic carbon atoms, or a heteroaromatic 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 H4--CO-- --CO--C.sub.6 H.sub.4 CO--, or --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.dbd.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 monofunctional acyl compound of the general formula
• YCOBD(R').sub.t or O(COBD(R').sub.t).sub.2
• or a di-functional acy 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 a 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 no 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) an inorganic salt controlling agent in an amount from 0.1 to 4 equivalents per equivalent of acid, ester or acid halide group in the reactants;
• (B) a Lewis acid selected from the group consisting of aluminum trichloride, aluminum tribromide, antimony pentachloride, antimony pentafluoride, indium trichloride, gallium trichloride, boron trichloride, boron trifluoride, ferric chloride, stannic chloride, titanium tetrachloride, and molybdenum pentachloride, in an amount of about one equivalent per equivalent of carbonyl, or other basic species in the reactants plus one equivalent per equivalent of Lewis base plus an amount effective to act as a catalyst for the reaction;
• and
• (C) a non-protic diluent in an amount from about 20 to about 93% by weight, based on the weight of the total reaction mixture.