Process for preparation of aromatic acid chlorides
AssigneeEastman Kodak Company
InventorsJohn A. Hyatt, David S. Kashdan
Life of this patent
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Abstract
Disclosed is a process for converting aromatic aldehydes to the corresponding acid chlorides by reacting an aromatic aldehyde with sulfuryl chloride in the presence of a catalytic amount of a phosphine, phosphine oxide or phosphonium compound. The product compounds produced by the process of this invention are useful as chemical synthesis intermediates in the preparation of pharmaceuticals, dyes, herbicides and photographic chemicals.
Claims20
Process for preparation of a compound having the formula ##STR6## which comprises reacting an aromatic aldehyde having the formula ##STR7## with sulfuryl chloride, wherein R.sup.1 is selected from the group consisting of hydrogen and alkyl of up to 8 carbon atoms, --(C.sub.6 H.sub.4)--CH.sub.3, --CHO and Z, wherein Z is an electron withdrawing group selected from the group consisting of --CN, --COCl, --SO.sub.2 (C.sub.6 H.sub.5), --SO(C.sub.6 H.sub.5), --N.dbd.N--C.sub.6 H.sub.5 and --CO.sub.2 R.sup.7 wherein R.sup.7 is alkyl of up to 8 carbon atoms;
- R.sup.2 is selected from the group consisting of hydrogen, alkyl of up to 8 carbon atoms, --(C.sub.6 H.sub.4)--CH.sub.3, --COCl and Z;
- the reaction being conducted in the presence of a catalytic amount of a compound having the formula ##STR8## wherein Y is selected from the group consisting of P, P=0, and ##STR9## wherein X is selected from the group consisting of chlorine and bromine;
- R.sup.8 is selected from the group consisting of chlorine, bromine and M;
- and M, R.sup.4, R.sup.5 and R.sup.6 are independently selected from the group consisting of alkyl and haloalkyl ##STR10## wherein R.sup.9 is an alkylene group containing up to 8 carbon atoms, n is an integer from 0 to 1;
- A is selected from the group consisting of chlorine, bromine and alkyl and haloalkyl containing up to 8 carbon atoms, and m is an integer from 0 to 5.
Process for preparation of a compound having the formula ##STR13## which comprises reacting an aromatic aldehyde having the formula ##STR14## with sulfuryl chloride, wherein R.sup.1 is selected from the group consisting of hydrogen and alkyl of up to 8 carbon atoms, --(C.sub.6 H.sub.4)--CH.sub.3, --CHO and Z, wherein Z is an electron withdrawing group selected from the group consisting of --CN, --COCl, --SO.sub.2 (C.sub.6 H.sub.5), --SO(C.sub.6 H.sub.5), --N.dbd.N--C.sub.6 H.sub.5 and --CO.sub.2 R.sup.7 wherein R.sup.7 is alkyl of up to 8 carbon atoms;
- R.sup.2 is selected from the group consisting of hydrogen, alkyl of up to 8 carbon atoms, --(C.sub.6 H.sub.4)--CH.sub.3, --COCl and Z;
- the reaction being conducted in the presence of a catalytic amount of triphenylphosphine or triphenylphosphine oxide.
Dependencies are inferred from the claim text.