US 5,510,506 A · Process for producing carboxylic acid derivatives

Abstract

A process is disclosed to produce a carboxylic acid derivative of the general formula VIII!: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and L are each as defined in the specification, characterized in that a benzyl halide is reacted with a cyano compound to give a phenylacetonitrile, which is then reacted with an alkyl nitrite in the presence of a base to give an .alpha.-hydroxyiminophenylacetonitrile, which is then reacted with an alkylating agent to give an .alpha.-alkoxyiminophenylacetonitrile, which is then hydrolyzed in the presence of a base, or is hydrated and treated with an acid, followed by hydrolysis in the presence of a base, to give an .alpha.-alkoxyiminophenylacetic acid, which is then reacted with an acid halide forming agent, or is convened into a metal salt, followed by reaction with an alkylating agent, or is reacted with a lower alcohol in the presence of an acid catalyst. According to the present invention, the reactions can be allowed to proceed under mild conditions over the whole process, and the desired carboxylic acid derivative VIII! can be produced without any facilities such as high-pressure steam equipment, high-temperature heat medium control equipment and freezing machines. In addition, there is no need to use various different solvents in the respective steps and the present process can be conducted with only one solvent, in which respect the present invention is also advantageous.

Claims12

Dependent claims

A process for producing a carboxylic acid derivative of the general formula VIII!:

##STR13## wherein R.sup.1, R.sup.2 and R.sup.3 are each as defined below and L is halogen or C.sub.1 -C.sub.5 alkoxy, characterized in that:
a benzyl halide of the general formula III!:
##STR14## wherein R.sup.1 and R.sup.2 are the same or different and are independently hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.2 -C.sub.4 alkenyl, halogen or trifluoromethyl, and X is halogen, is reacted with a cyano compound to give a phenylacetonitrile of the general formula IV!:
##STR15## wherein R.sup.1 and R.sup.2 are each as defined above;
this compound is reacted with an alkyl nitrite in the presence of a base to give an .alpha.-hydroxyiminophenylacetonitrile of the general formula V!:
##STR16## wherein R.sup.1 and R.sup.2 are each as defined above and A is an alkali metal or an alkaline earth metal;
this compound is reacted with an alkylating agent to give an .alpha.-alkoxyiminophenylacetonitrile of the general formula VI!:
##STR17## wherein R.sup.1 and R.sup.2 are each as defined above and R.sup.3 is C.sub.1 -C.sub.5 alkyl;
this compound is hydrolyzed in the presence of a base, or this compound is hydrated and treated with an acid, followed by hydrolysis in the presence of a base, to give an .alpha.-alkoxyiminophenylacetic acid of the general formula VII! ##STR18## wherein R.sup.1, R.sup.2 and R.sup.3 are each as defined above;
and this compound is reacted with an acid halide forming agent, or converted into a metal salt and then reacted with an alkylating agent, or reacted with a lower alcohol in the presence of an acid catalyst.

7 more elements

Dependencies are inferred from the claim text.

Process for producing carboxylic acid derivatives

Life of this patent

Process for producing carboxylic acid derivatives

Life of this patent

Abstract

Claims12