Process for synthesizing benzoic acids

A process for the preparation of a compound of formula (III) comprising the steps of

• (i) reacting a compound of formula (I) with an alkali or alkaline earth metal cyanide, an aldehyde or ketone cyanohydrin or hydrogen cyanide in the presence of a catalyst comprising nickel, cobalt, palladium or platinum, or reacting a compound of formula (I) with copper(I) cyanide in the optional presence of a catalyst comprising nickel, cobalt, palladium or platinum to form an aromatic cyano compound of formula (IIb) ##STR14## (ii) reacting a compound of formula (IIb) with an alkali or alkaline earth alkoxide, alkali or alkaline earth aroxide, alkali or alkaline earth arylalkoxide, or alkali or alkaline earth heteroarylalkoxide, optionally in the presence of a catalyst comprising copper, to provide a compound of formula (III) ##STR15## wherein each X is independently triflyl,
• R is a hydrogen atom, (C.sub.1 -C.sub.6)alkyl, aryl, aryl(C.sub.1 -C.sub.2)alkyl, heteroaryl or heteroaryl(C.sub.1 -C.sub.2)alkyl;
• or a (C.sub.1 -C.sub.6)alkyl, aryl, aryl(C.sub.1 -C.sub.2)alkyl, heteroaryl or heteroaryl(C.sub.1 -C.sub.2)alkyl substituted with from one to three substituents independently selected from (C.sub.1 -C.sub.3)alkyl and (C.sub.1 -C.sub.3)alkoxy;
• R.sup.1 is CHR.sup.2 R.sup.3, aryl, aryl(C.sub.1 -C.sub.2)alkyl or heteroaryl(C.sub.1 -C.sub.2)alkyl;
• or aryl, aryl(C.sub.1 -C.sub.2)alkyl or heteroaryl(C.sub.1 -C.sub.2)alkyl substituted with from one to three substituents independently selected from (C.sub.1 -C.sub.3)alkyl and (C.sub.1 -C.sub.3)alkoxy;
• and
• R.sup.2 and R.sup.3 are each independently a hydrogen atom, (C.sub.1 -C.sub.5)alkyl or (C.sub.1 -C.sub.3)alkyl substituted with (C.sub.1 -C.sub.2)alkoxy.

A process for the preparation of a compound of formula (III) comprising reacting a compound of formula (IIa) with an alkali or alkaline earth metal cyanide, an aldehyde or ketone cyanohydrin or hydrogen cyanide in the presence of a catalyst comprising nickel, cobalt, palladium or platinum, or reacting a compound of formula (IIa) with copper(I) cyanide in the optional presence of a catalyst comprising nickel, cobalt, palladium or platinum to form an aromatic cyano compound of formula (III) ##STR24## wherein X is triflyl;

• R is a hydrogen atom, (C.sub.1 -C.sub.6)alkyl, aryl, aryl(C.sub.1 -C.sub.2)alkyl, heteroaryl or heteroaryl(C.sub.1 -C.sub.2)alkyl;
• or a (C.sub.1 -C.sub.6)alkyl, aryl, aryl(C.sub.1 -C.sub.2)alkyl, heteroaryl or heteroaryl(C.sub.1 -C.sub.2)alkyl substituted with from one to three substittuents independently selected from (C.sub.1 -C.sub.3)alkyl and (C.sub.1 -C.sub.3)alkoxy;
• R.sup.1 is CHR.sup.2 R.sup.3, aryl, aryl(C.sub.1 -C.sub.2)alkyl or heteroaryl(C.sub.1 -C.sub.2)alkyl;
• or aryl, aryl(C.sub.1 -C.sub.2)alkyl or heteroaryl(C.sub.1 -C.sub.2)alkyl substituted with from one to three substituents independently selected from (C.sub.1 -C.sub.3)alkyl and (C.sub.1 -C.sub.3)alkoxy;
• and
• R.sup.2 and R.sup.3 are each independently a hydrogen atom, (C.sub.1 -C.sub.5)alkyl or (C.sub.1 -C.sub.3)alkyl substituted with (C.sub.1 -C.sub.2)alkoxy.

A process for the preparation of a compound of formula (III) comprising reacting a compound of formula (IIb) with an alkali or alkaline earth alkoxide, alkali or alkaline earth aroxide, alkali or alkaline earth arylalkoxide, or alkali or alkaline earth heteroarylalkoxide, optionally in the presence of a catalyst comprising copper, to provide a compound of formula (III) ##STR25## wherein X is triflyl;

• R is a hydrogen atom, (C.sub.1 -C.sub.6)alkyl, aryl, aryl(C.sub.1 -C.sub.2)alkyl, heteroaryl or heteroaryl(C.sub.1 -C.sub.2)alkyl;
• or a (C.sub.1 -C.sub.6)alkyl, aryl, aryl(C.sub.1 -C.sub.2)alkyl, heteroaryl or heteroaryl(C.sub.1 -C.sub.2)alkyl substituted with from one to three substituents independently selected from (C.sub.1 -C.sub.3)alkyl and (C.sub.1 -C.sub.3)alkoxy;
• R.sup.1 is CHR.sup.2 R.sup.3, aryl, aryl(C.sub.1 -C.sub.2)alkyl or heteroaryl(C.sub.1 -C.sub.2)alkyl;
• or aryl, aryl(C.sub.1 -C.sub.2)alkyl or heteroaryl(C.sub.1 -C.sub.2)alkyl substituted with from one to three substituents independently selected from (C.sub.1 -C.sub.3)alkyl and (C.sub.1 -C.sub.3)alkoxy;
• and
• R.sup.2 and R.sup.3 are each independently a hydrogen atom, (C.sub.1 -C.sub.5)alkyl or (C.sub.1 -C.sub.3)alkyl substituted with (C.sub.1 -C.sub.2)alkoxy.