CA2207583A1 - Process for the production of 2-(substituted benzoyl)1,3 cyclohexanediones - Google Patents
Process for the production of 2-(substituted benzoyl)1,3 cyclohexanedionesInfo
- Publication number
- CA2207583A1 CA2207583A1 CA002207583A CA2207583A CA2207583A1 CA 2207583 A1 CA2207583 A1 CA 2207583A1 CA 002207583 A CA002207583 A CA 002207583A CA 2207583 A CA2207583 A CA 2207583A CA 2207583 A1 CA2207583 A1 CA 2207583A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- haloalkyl
- hydrogen
- alkoxy
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 2-(substituted benzoyl)1,3 cyclohexanediones Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000012454 non-polar solvent Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for preparing a compound of formula (I), where R1, R2, R3 R4, R5 and R6 are independently hydrogen or C1-6 alkyl; R7 is halogen, cyano, NO2, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or RaS in which Ra is C1-4 alkyl; R8, R9 and R10 independently are hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, CN, NO2, phenoxy or substituted phenoxy;
R b S(O)n Om in which m is 0 or 1, n is 0, 1 or 2 and Rb is C1-4 alkyl, C1-4 haloalkyl, phenyl or benzyl, NHCOR c in which Rc is C1-4 alkyl, NRdRe in which Rd and Re indenpendently are hydrogen or C1-4 alkyl; RfC(O)- in which Rf is hydrogen, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy; SO2NRgRh in which Rg and Rh independently are hydrogen or C1-4 alkyl; or any two of R8, R9 and R10 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 =NOC1-4 alkyl, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or halogen; which process comprises the rearrangement of a compound of formula (II) where R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are as defined in relation to formula (I), in a non-polar solvent in the presence of a cyanide source, an alkali or alkaline earth metal carbonate, a phase transfer catalyst and 1-6 moles of water with respect to the compound of formula (II).
R b S(O)n Om in which m is 0 or 1, n is 0, 1 or 2 and Rb is C1-4 alkyl, C1-4 haloalkyl, phenyl or benzyl, NHCOR c in which Rc is C1-4 alkyl, NRdRe in which Rd and Re indenpendently are hydrogen or C1-4 alkyl; RfC(O)- in which Rf is hydrogen, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy; SO2NRgRh in which Rg and Rh independently are hydrogen or C1-4 alkyl; or any two of R8, R9 and R10 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 =NOC1-4 alkyl, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or halogen; which process comprises the rearrangement of a compound of formula (II) where R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are as defined in relation to formula (I), in a non-polar solvent in the presence of a cyanide source, an alkali or alkaline earth metal carbonate, a phase transfer catalyst and 1-6 moles of water with respect to the compound of formula (II).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9501434.6 | 1995-01-25 | ||
| GBGB9501434.6A GB9501434D0 (en) | 1995-01-25 | 1995-01-25 | Chemical process |
| PCT/GB1996/000082 WO1996022958A1 (en) | 1995-01-25 | 1996-01-16 | Process for the production of 2-(substituted benzoyl)1,3 cyclohexanediones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2207583A1 true CA2207583A1 (en) | 1996-08-01 |
| CA2207583C CA2207583C (en) | 2006-12-12 |
Family
ID=37561058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002207583A Expired - Fee Related CA2207583C (en) | 1995-01-25 | 1996-01-16 | Process for the production of 2-(substituted benzoyl)1,3 cyclohexanediones |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2207583C (en) |
-
1996
- 1996-01-16 CA CA002207583A patent/CA2207583C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2207583C (en) | 2006-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150116 |