Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1999-06-21
2000-11-14
O'Sullivan, Peter
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
568315, 568337, C07C24904, C07C 4546, C07C24908
Patent
active
061472603
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a chemical process.
European Patent No. 85529 discloses a class of 2-[1-(alkoxyimino)-alkyl]-5-(substituted phenyl) cyclohexane-1,3-dione derivatives useful as selective herbicides.
A compound of this class, 5-(3-butyryl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)propyl]-3-hydroxycyc lohex-2-en-1-one, having the structural formula (1), has been found to be particularly useful in the selective control of graminaceous weeds.
European Patent No. 85529 describes the preparation of compounds of this type (although the compound of formula (I) is not itself disclosed).
PCT Appplication No WO 92/21649 discloses a process for making the compound of formula (I) by the reaction of butyryl chloride with a compound of formula (III).
The present invention provides an alternative process for preparation of the compound of formula (I).
According to the present invention, therefore, there is provided a process of preparing a compound of formula (I) which comprises reacting a compound of formula (IV) with butyryl chloride in the presence of a Friedel-Crafts reaction catalyst, in an inert diluent to produce a compound of formula (II) and reacting the compound of formula (II) with ethoxyamine. Suitable Friedel-Crafts catalysts include aluminium chloride, ferric chloride and mixtures of aluminium chloride and ferric chloride. Preferably the Friedel-Crafts catalyst is anhydrous aluminium chloride. The Friedel-Crafts catalyst is used in an amount of from 1 to 10 molar proportions with respect to the compound of formula (IV), and preferably from 3 to 5 molar proportions. The butyryl chloride is used in an amount of from 1 to 10 molar proportions and preferably from 1.5 to 2.5 molar proportions with respect to the compound of formula (IV).
The diluent used in the reaction of the compound of formula (IV) with butyryl chloride may be selected from those diluents known to be used in Friedel-Crafts reactions. It may for example be a hydrocarbon or a chlorinated hydrocarbon, or a nitro-hydrocarbon. Examples of suitable aliphatic and alicyclic hydrocarbons include the mixture of aliphatic hydrocarbons sold under the trade name Isopar M, which has a boiling range of 210-250.degree. C., n-pentane, n-heptane, n-hexane, cycloheptane and cyclohexane. Chlorinated hydrocarbons include, for example, dichloromethane and tetrachloroethylene.
Nitro-hydrocarbons include, for example, nitrobenzene and nitromethane.
The reaction is preferably carried out at a temperature in the range from -10 to 100.degree. C. and more preferably in the range 10 to 50.degree. C.
In the reaction of the compound of formula (II) with ethoxyamine, the ethoxyamine is used in an amount of from 0.5 to 5 molar proportions with respect to the compound of formula (II), and preferably from 1.0 to 2.0 molar proportions.
The reaction is preferably carried out at a temperature in the range from 0 to 80.degree. C. and more preferably in the range 20 to 50.degree. C.
The reaction is suitably carried out in a solvent such as 2-propanol, cyclohexane, n-heptane, n-octane, or an aromatic hydrocarbon such as xylene or toluene.
Preferred solvents are n-heptane or 2-propanol.
The reaction may also be carried out in the presence of a catalyst. Suitable catalyst includes organo-tin compounds such as dibutyltin diacetate.
The order of addition of the reactants may be varied as required. For example the butyryl chloride may be added to the compound of formula (IV) and the Friedel Crafts catalyst in a solvent, or the butyryl chloride may be added to a slurry of the Friedel Crafts catalyst followed by addition of the compound of formula (IV) as a solution.
The compound 5-(3-butyryl-2,4,6-trimethylphenyl)-3-hydroxy-2-propionylcyclohex-2-en-1-o ne having the structural formula (II) is novel and as such forms a further aspect of the invention.
The compound of formula (IV), 3-hydroxy-2-propionyl-5-(2,4,6-trimethylphenyl)cyclohex-2-en-1-one is a known compound.
It is has surprisingly been found that performing the Friedel Crafts reaction before the oximation reaction greatly i
Bird Graham John
Watson Keith Geoffrey
O'Sullivan Peter
Orica Australia PTY LTD
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