Preparation of imidazolinyl benzoic acids, esters and salts

A method for the preparation of a compound having the formula:

• ##STR89## wherein X is hydrogen, alkyl C.sub.1 -C.sub.3, halogen or nitro;
• R.sub.1 is alkyl C.sub.1 -C.sub.4 ;
• R.sub.2 is alkyl C.sub.1 -C.sub.6, cycloalkyl C.sub.3 -C.sub.6, alkenyl C.sub.2 -C.sub.4, phenyl, halophenyl or benzyl or when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached they may represent cycloalkyl C.sub.3 -C.sub.6 optionally substituted with methyl;
• R.sub.3 is, alkyl C.sub.1 -C.sub.12 optionally substituted with one C.sub.1 -C.sub.3 alkoxy group or one C.sub.3 -C.sub.6 cycloalkyl group or one phenyl group or one furyl group, alkenyl C.sub.3 -C.sub.5 optionally substituted with one or two C.sub.1 -C.sub.3 alkyl group(s) or one phenyl group or with one to two halogen substituent(s) alkynyl C.sub.3 -C.sub.5 optionally substituted with one or two C.sub.1 -C.sub.3 alkyl group(s) or one phenyl group or with one to two halogen substituent(s), benzyl, cyclohexenylmethyl, ethynylcyclohexyl, ethynylalkyl or pentadienyl, cycloalkyl, C.sub.3 -C.sub.6 optionally substituted with one or two C.sub.1 -C.sub.3 alkyl group(s);
• and when R.sub.1 and R.sub.2 are not the same the optical isomers thereof, and the isomeric mixtures thereof;
• comprising, reacting a compound having the formula:
• ##STR90## wherein X, R.sub.1 and R.sub.2 are as described above, which an alcohol having the formula:
• R.sub.3 OH where R.sub.3 is described above, in the presence of an alkali metal or alkali metal hydride and at a temperature between about 20.degree. C. and 50.degree. C.