Process for producing carboxylic acid derivatives

Details Process for producing carboxylic acid derivatives Process for producing carboxylic acid derivatives

1995-03-27

1996-04-23

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C07C22902

Patent

active

055105068

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP94/01075.


TECHNICAL FIELD

The present invention relates to a process for producing carboxylic acid derivatives of the general formula VIII!: ##STR2## 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, R.sup.3 is C.sub.1 -C.sub.5 alkyl, and L is halogen or C.sub.1 -C.sub.5 alkoxy.


BACKGROUND ART

The carboxylic acid derivatives VIII! are useful as agricultural fungicides or their intermediates (JP-A 4-295454), and as the process for their production, it has been known that they can be produced by the following route in which metal salts of phenol derivatives of the general formula I!: ##STR3## wherein R.sup.1 and R.sup.2 are each as defined above and A is an alkali metal or an alkaline earth metal, are used as the staring material (JP-A 4-295454): ##STR4##
However, when the carboxylic acid derivatives VIII! are produced by such a process, the reaction in the step (i) is effected at a high temperature such as 200.degree. C., which requires factory facilities for use as a heating source, such as high-pressure steam equipment or high-temperature heat medium control equipment, or the reaction in the step (iv) is effected under cooling below 0.degree. C., which requires various facilities such as freezing machines. This process is, therefore, not a satisfactory process from an industrial point of view.
Further, in this process, different solvents are used in the respective steps: for example, methanol in the step (i); toluene in the steps (ii) and (iii); methyl t-butyl ether and methanol (reaction solvent) as well as dichloromethane (extraction solvent) in the step (iv); and methanol and dichloromethane (reaction solvent) in the step (v). In addition to such a complicated feature that various kinds of solvents are used in the production on an industrial scale, there is another disadvantage that it requires solvent recovery facilities and numerous solvent storage tanks, in which respect the above process is not satisfactory as an industrial production process.


DISCLOSURE OF THE INVENTION

The present inventors have extensively studied to develop an industrially favorable route for production of carboxylic acid derivatives VIII!. As a result, they have found a quite novel route for production of carboxylic acid derivatives VIII! where the respective reactions can be allowed to proceed under mild reaction conditions, for example, at temperatures of from room temperature to about 150.degree. C. As a result of further studies, they have found that this route makes it possible to use only one solvent without using various different solvents in the respective steps, thereby completing the present invention.
Thus, the present invention provides a process for producing a carboxylic acid derivative of the general formula VIII!: ##STR5## 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!: ##STR6## 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!: ##STR7## 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!: ##STR8## 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!: ##STR9## 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, trea

REFERENCES:
patent: 4233233 (1980-11-01), Schroer
patent: 4466822 (1984-08-01), Martin
patent: 5221762 (1993-06-01), Wingert
patent: 5354883 (1994-10-01), Isak

Affiliated with

Also associated with

Rating

Process for producing carboxylic acid derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for producing carboxylic acid derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing carboxylic acid derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2309794