WO1993013060A1 - Nouveaux composes intermediaires et leur production - Google Patents
Nouveaux composes intermediaires et leur production Download PDFInfo
- Publication number
- WO1993013060A1 WO1993013060A1 PCT/JP1992/001687 JP9201687W WO9313060A1 WO 1993013060 A1 WO1993013060 A1 WO 1993013060A1 JP 9201687 W JP9201687 W JP 9201687W WO 9313060 A1 WO9313060 A1 WO 9313060A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- general formula
- formula
- production
- compound represented
- novel intermediate
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- -1 2-(substituted benzoyl)-1,3-cyclohexanedione compound Chemical class 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- 230000002363 herbicidal effect Effects 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- HPXOTHKSLCMBPG-UHFFFAOYSA-N 2-methoxy-1-methyl-3-methylsulfanylbenzene Chemical compound COc1c(C)cccc1SC HPXOTHKSLCMBPG-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical group O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
Definitions
- the present invention relates to a novel intermediate compound and a method for producing the same, and a method for producing another intermediate using the intermediate compound. These intermediates are useful as intermediates for agrochemicals.
- An object of the present invention is to provide a novel intermediate compound, a method for producing the same, and a method for producing a substituted benzoic acid using the intermediate.
- the present invention is a.
- This is a method for producing the compound represented by The production method of the present invention is as follows.
- the reaction from the formulas ( ⁇ ) to (I) is a Friedel-Crafts reaction, which is carried out in a solvent such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, carbon disulfide, and benzene. 2, the presence of S nC ⁇ 4, T i C ⁇ 4, AC 3 , etc. Lewis acids, is carried out at a temperature from 0 ° C to the boiling point of the solvent. Preferably Zn C £ 2.
- the reaction of the formula ( ⁇ ) force is a Ha 10 f 0 rm reaction and an oxidation reaction, and in an inert solvent such as dioxane as a solvent, a halogenating agent and an oxidizing agent such as NaBrO,
- the reaction temperature is from room temperature to the boiling point of the solvent using Na IO, KC ⁇ O, NaC £ 0 aqueous solution, or the like.
- a novel intermediate compound can be obtained in a high yield.
- a substituted benzoic acid can be industrially advantageously obtained.
- This substituted benzoic acid is useful as an intermediate of a herbicide shown in W091 / 0260. Japanese Patent Application No. 3-193595.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Composé représenté par la formule générale (I), qui représente un nouvel intermédiaire pour la synthèse d'un composé 2-(benzoyle substitué)-1,3-cyclohexanedione utile comme herbicide; procédé de production de ce composé; et procédé de production d'un composé intermédiaire représenté par la formule générale (III) à partir du composé de la formule (I), où R1 à R4 peuvent être identiques ou différents l'un de l'autre et représentent chacun alkyle inférieur.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3/356447 | 1991-12-25 | ||
| JP35644791A JPH05170730A (ja) | 1991-12-25 | 1991-12-25 | 新規な中間体化合物及びその製法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993013060A1 true WO1993013060A1 (fr) | 1993-07-08 |
Family
ID=18449057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1992/001687 WO1993013060A1 (fr) | 1991-12-25 | 1992-12-24 | Nouveaux composes intermediaires et leur production |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPH05170730A (fr) |
| WO (1) | WO1993013060A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997028122A3 (fr) * | 1996-02-01 | 1997-10-02 | Rhone Poulenc Agrochimie | Procede de preparation de composes dicetoniques |
| EP2546240A1 (fr) | 2005-12-15 | 2013-01-16 | Ishihara Sangyo Kaisha, Ltd. | Composés de benzoylpyrazole et herbicides les contenant |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61207369A (ja) * | 1985-03-07 | 1986-09-13 | ストウフアー ケミカル カンパニー | ３つの置換基を有する安息香酸中間体 |
-
1991
- 1991-12-25 JP JP35644791A patent/JPH05170730A/ja active Pending
-
1992
- 1992-12-24 WO PCT/JP1992/001687 patent/WO1993013060A1/fr active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61207369A (ja) * | 1985-03-07 | 1986-09-13 | ストウフアー ケミカル カンパニー | ３つの置換基を有する安息香酸中間体 |
Non-Patent Citations (1)
| Title |
|---|
| By SANDRO CARO, "Method for Synthesizing Organic Compounds by Functional Group (I)", 25 March 1976, Hirokawa Shoten (Tokyo), p. 183. * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997028122A3 (fr) * | 1996-02-01 | 1997-10-02 | Rhone Poulenc Agrochimie | Procede de preparation de composes dicetoniques |
| US6235942B1 (en) | 1996-02-01 | 2001-05-22 | Rhone-Poulenc Agrochimie | Process for preparing diketone compounds |
| US6525225B2 (en) | 1996-02-01 | 2003-02-25 | Rhone Poulenc Agrochimie | Process for preparing diketone compounds and precursors thereto |
| US6696613B2 (en) | 1996-02-01 | 2004-02-24 | Rhone Poulenc Agrochimie | Process for preparing diketone compounds and precursors thereto |
| EP2546240A1 (fr) | 2005-12-15 | 2013-01-16 | Ishihara Sangyo Kaisha, Ltd. | Composés de benzoylpyrazole et herbicides les contenant |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05170730A (ja) | 1993-07-09 |
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