Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1995-05-11
1997-05-13
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
C07C25501
Patent
active
056294425
DESCRIPTION:
BRIEF SUMMARY
This applications is 371 of PCT/JP94/01076 filed Jul. 1, 1994.
TECHNICAL FIELD
The present invention relates to a process for producing .alpha.-hydroxyimino- phenylacetonitriles.
BACKGROUND ART
.alpha.-Hydroxyiminophenylacetonitriles are known as intermediates of plant growth promoting agents, agricultural fungicides, or the like (e.g., Japanese Patent Publication No. 62-54096).
As the process of their production, for example, it is also known that .alpha.-hydroxyiminophenylacetonitriles are produced by reacting phenylacetonitriles with alkyl nitrites in an alcohol solvent in the presence of an aqueous base solution, then neutralizing with an acid, removing low-boiling contents by distillation, and collecting the precipitated solids by filtration (e.g., Japanese Patent Laid-open Publication No. 54-163548).
In the case where crude starting materials containing impurities are used as the starting material phenylacetonitriles, however, there is a difficult point that .alpha.-hydroxyiminophenylacetonitriles as the desired products have a decreased purity, if produced by the above process.
In the case where crude materials are used after being purified by distillation or other techniques, there is also a difficult point that complicated steps for separation and purification are required and the yield is decreased by their operations or the like.
DISCLOSURE OF THE INVENTION
The present inventors have extensively studied to develop a more favorable process for producing .alpha.-hydroxyiminophenylacetonitriles by use of crude phenylacetonitriles. As a result, they have found that the desired .alpha.-hydroxyiminophenylacetonitriles can be produced with high purity, in high yield and with ease by reacting the crude phenylacetonitriles with alkyl nitrites, extracting the reaction mass with water, and then neutralizing the separated aqueous layer with an acid, and they have further made various studies, thereby completing the present invention.
Thus, the present invention provides an industrially favorable process for producing an .alpha.-hydroxyiminophenylacetonitrile of the general formula [II]: ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 and Z are each as defined below, characterized in that a crude nitrile containing a phenylacetonitrile of the general formula [I]: ##STR4## wherein R.sup.1, R.sup.2 and R.sup.3 are the same or different and are independently hydrogen, halogen, nitro, trifiuoromethyl, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy, and Z is --O--, --OCH.sub.2 --, --S-- or --SCH.sub.2 --, is reacted with an alkyl nitrite; extracting the reaction mixture with water; and then neutralizing the separated aqueous layer with an acid.
The present invention will hereinafter be explained in detail.
As the substituents R.sup.1, R.sup.2 and R.sup.3 of the phenylacetonitrile [I] as the starting material component of the present invention, there can be mentioned, for example, hydrogen; halogen such as fluorine, chlorine, bromine and iodine; nitro; trifluoromethyl; C.sub.1 -C.sub.5 alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl and pentyl; and C.sub.1 -C.sub.5 alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentyloxy, and the like.
As the Z, there can be mentioned oxygen, oxymethylene, sulfur, thiomethylene, and the like.
As the specific compound of the phenylacetonitrile [I], there can be mentioned, for example, 2-phenoxyphenylacetonitrile, 3-phenoxyphenylacetonitrile, 4-phenoxyphenylacetonitrile, 2-(2-fluorophenoxy)phenylacetonitrile, 4-(3-chlorophenoxy)phenylacetonitrile, 3-(4-bromophenoxy)phenylacetonitrile, 3-(3-nitrophenoxy)phenylacetonitrile, 2-(4-nitrophenoxy)phenylacetonitrile , 2-(2-methoxyphenoxy)phenylacetonitrile, 4-(3-methoxyphenoxy)phenylacetonitrile, 3-(2-ethoxyphenoxy)phenylacetonitrile, 4-(2-isopropoxyphenoxy)phenylacetonitrile, 4-(4-butoxyphenoxy)phenylacetonitrile, 3-(2-methoxy-5-nitrophenoxy)phenylacetonitrile, 2-(2,3-dimethoxyphenoxy)phenylacetonitrile, 2-(3,4,5-trimethoxyphenoxy)phenylacetonitrile, 2-(phenylthio)phe
REFERENCES:
patent: 4233233 (1980-11-01), Schroer et al.
Kai Hiroyuki
Kiyoshima Yujiro
Masui Moriyasu
Masumoto Katuhisa
Nakamura Akihiko
Peabody John
Richter Johann
Shionogi & Co. Ltd.
Sumitomo Chemical Company Ltd.
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