Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-06-24
1998-03-17
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568308, C07C 4923, C07C 49213
Patent
active
057288895
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to the production of 2-(substituted benzoyl)-1,3-cyclohexanedione compounds.
2-(substituted benzoyl)-1,3-cyclohexanediones are known as herbicides from for example U.S. Pat. No. 4,780,127, U.S. Pat. No. 4,806,146, U.S. Pat. No. 4,946,981, U.S. Pat. No. 5,006,158, WO 9408988 and WO 9404524. One method of producing these compounds is by re-arrangement of an enol ester. This method is described in U.S. Pat No. 4,780,127 and U.S. Pat. No. 4,695,673. In these rearrangement reactions the presence of hydrogen cyanide or cyanide anion is described as essential (generally in an amount of 1-10 mol percent with respect to the enol ester). In an industrial scale process it is desirable to avoid the use of such materials. Surprisingly it has now been found that in certain solvents it is possible to perform the rearrangement in the absence of hydrogen cyanide or cyanide anion.
According to the present invention there is provided a process for preparing a compound of formula (I) where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen or C.sub.1-6 alkyl; R.sup.7 is halogen, cyano, NO.sub.2, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or RaS in which Ra is C.sub.1-4 alkyl; R.sup.8, R.sup.9 and R.sup.10 independently are hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkyl, CN, NO.sub.2, phenoxy or substituted phenoxy; R.sub.b S(O)nOm in which m is 0 or 1, n is 0, 1 or 2 and Rb is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, phenyl or benzyl, NHCOR.sub.c in which Rc is C.sub.1-4 alkyl, NRdRe in which Rd and Re independently are hydrogen or C.sub.1-4 alkyl; RfC(O)-- in which Rf is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl or C.sub.1-4 alkoxy; SO.sub.2 NRgRh in which Rg and Rh independently are hydrogen or C.sub.1-4 alkyl; or any two of R.sup.8, R.sup.9 and R.sup.10 together with the carbon atoms to which they are attached form a 5 or 6 membered heterocyclic ring containing up to three heteroatoms selected from O, N or S and which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, .dbd.NOC.sub.1-4 alkyl or halogen; which process comprises the rearrangement of a compound of formula (II) where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as defined in relation to formula (I), in the presence of a base and a polar aprotic solvent characterised in that the process is carried out in a reaction medium substantially free of hydrogen cyanide or cyanide anion.
As used herein the term "alkyl", refers to straight or branched chains. The term "haloalkyl" refers to an alkyl group substituted by at least one halogen. Similarly the term "haloalkoxy" refers to an alkoxy group substituted by at least one halogen. As used herein the term "halogen" refers to fluorine, chlorine, bromine and iodine.
Suitable optional substituents for phenoxy groups R.sup.8, R.sup.9 and R.sup.10 include halogen such as fluorine and chlorine and C.sub.1-4 haloalkyl.
A preferred group of compounds of formula (I) are those where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen or C.sub.1-6 alkyl; R.sup.7 is halogen, cyano, NO.sub.2, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or RaS in which Ra is C.sub.1-4 alkyl; R.sup.8, R.sup.9 and R.sup.10 independently are hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, CN, NO.sub.2, phenoxy or substituted phenoxy; R.sub.b S(O)nOm in which m is 0 or 1, n is 0, 1 or 2 and Rb is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, phenyl or benzyl, NHCOR.sub.c in which Rc is C.sub.1-4 alkyl, NRdRe in which Rd and Re independently are hydrogen or C.sub.1-4 alkyl; RfC(O)-- in which Rf is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl or C.sub.1-4 alkoxy; or SO.sub.2 NRgRh in which Rg and Rh independently are hydrogen or C.sub.1-4 alkyl.
Preferably R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen or C.sub.1-4 alkyl. More p
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Brown Stephen Martin
Rawlinson Howard
Wiffen Jonathan William
Geist Gary
Puttlitz, Jr. Karl J.
Snyder Joseph R.
Zeneca Limited
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