Fluorine-substituted phenyl benzoates and process for producing

Details Fluorine-substituted phenyl benzoates and process for producing Fluorine-substituted phenyl benzoates and process for producing

1986-06-05

1987-11-10

Killos, Paul J.

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

Organic compounds

Carboxylic acid esters

C07C 6976

Patent

active

047058846

DESCRIPTION:

BRIEF SUMMARY
FIELD OF TECHNOLOGY

This invention relates to new substituted benzoic acid derivatives. More specifically, the invention relates to fluorine-substituted phenyl benzoates having the general formula other is m-fluorophenyl group, as well as a process for producing these phenyl benzoates.
The fluorine-substituted phenyl benzoates of the general formula (I) can be used as a starting material for producing the fluorophenols, which are valuable as intermediates for synthesizing medicines, agricultural drugs or functional materials. Specifically, the fluorophenols can be easily derived from the compounds of general formula (I) by hydrolysis.


PRIOR ART

Known heretofore as processes for producing the fluorophenols are say (a) that of subjecting fluoroaniline to the Sandmeyer reaction [Ger. Offen No. 2,426,994 (1975)]; (b) that of subjecting aminophenol to the Schiemann reaction [Dunker, M. F. W.; Starkey, E. B., J. Am. Chem, Soc., 1939, 11, 3005 and Finger, G. C.; Oesterling, R. E., J. Am. Chem. Soc., 1956, 78, 2593]; (c) that of hydrolyzing bromofluorobenzene [Boudakian, M. M.; Eber, R. J.; McArthur, R. E., J. Org. Chem., 1961, 26, 4641]; and (d) that of subjecting fluoroanisole to acid decomposition [Suter, C. M.; Lawson, E. J.; Smith, P. G., J. Am. Chem. Soc., 1939, 61, 165]. These conventional processes have however the following defects. In the case of the process of (a) not only is there the problem of procuring the starting material, but also a large amount of an acid such as sulfuric acid must be used. The process of (b) requires the use of borofluoric acid of high purity, which cannot be reused. Not only are the reaction conditions harsh in the case of process of (c), but also there is the possibility of a defluorination reaction taking place concurrently, as well as a tendency to the formation as a by-product of unsubstituted phenol, whose separation from the fluorophenols is difficult. On the other hand, in the case of the process of (d), the starting materials other than p-fluoroanisole are not readily available, and hence the process is restricted to the synthesis of only the p-isomer of the fluorophenols.
The conventional processes thus had their shortcomings in that the fluorophenols could not be produced by a simple and convenient process or that it was not possible to produce the fluorophenol isomers, as desired. They were thus not employable on an industrial scale.


DISCLOSURE OF THE INVENTION

Extensive investigations were made by the present inventors for an industrially feasible process for producing the fluorophenols. These investigations led to the discovery of the fluorine-substituted phenyl benzoates of general formula (I), a precursor of the fluorophenols, and to the perfection of an industrially advantageous process for its production.
The fluorine-substituted phenyl benzoates of general formula (I) provided by the present invention can be easily produced by subjecting to an oxidative decarboxylation reaction a fluorobenzoic acid of the general formula
Fluorobenzoic acid of general formula (II) used in the above reaction is a compound known per se. For example, it is a compound that can be obtained easily at low cost by the oxidation of fluorotoluene.
The oxidative decarboxylation reaction of the fluorobenzoic acid of general formula (II) can usually be carried out by bringing the fluorobenzoic acid into contact with an oxidizing agent in a solventless state or preferably in an inert organic solvent having a relative high boiling point (preferably ranging from 180.degree. to 260.degree. C.) and capable of being refluxed at the reaction temperature, such as diethyl fumarate, diphenyl ether, tetraglyme and decalin. Usable in this case as the oxidizing agent are, for example, the cupric salts and such combinations as oxygen and a catalytic amount of copper, cuprous or cupric salt, or copper oxide. Examples of usable copper or copper salts include copper powder and porous copper; cuprous halide and cupric halide; organic acid salts of copper such as copper fluorobenzoate and copper aceta

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