JPS6272681A - ピレスロイド中間体製造の新規な方法 - Google Patents
ピレスロイド中間体製造の新規な方法Info
- Publication number
- JPS6272681A JPS6272681A JP60214414A JP21441485A JPS6272681A JP S6272681 A JPS6272681 A JP S6272681A JP 60214414 A JP60214414 A JP 60214414A JP 21441485 A JP21441485 A JP 21441485A JP S6272681 A JPS6272681 A JP S6272681A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- formula
- aqueous
- temperature
- cis
- 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
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000002728 pyrethroid Substances 0.000 title description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 238000005658 halogenation reaction Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical group 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 239000004210 ether based solvent Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 description 7
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848424561A GB8424561D0 (en) | 1984-09-28 | 1984-09-28 | (1r cis) - 4 - acetyl - 6 6 - dimethyl - 3 - oxabicyclo-(3 1 0) hex - 2 - one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6272681A true JPS6272681A (ja) | 1987-04-03 |
| JPH0574590B2 JPH0574590B2 (en, 2012) | 1993-10-18 |
Family
ID=10567414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60214414A Granted JPS6272681A (ja) | 1984-09-28 | 1985-09-27 | ピレスロイド中間体製造の新規な方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4680418A (en, 2012) |
| EP (1) | EP0180325B1 (en, 2012) |
| JP (1) | JPS6272681A (en, 2012) |
| DE (1) | DE3565264D1 (en, 2012) |
| GB (1) | GB8424561D0 (en, 2012) |
| IN (1) | IN162785B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5228249A (en) * | 1991-04-12 | 1993-07-20 | Campbell Carl W | Wooden foundation wall and method |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2052479B (en) * | 1979-04-06 | 1983-04-07 | Shell Int Research | Bicyclohexane compound useful as an intermediate in the preparation of pyrethroid insecticides |
| US4257956A (en) * | 1979-04-06 | 1981-03-24 | Shell Oil Company | Oxabicycloalkane pyrethroid intermediates |
| US4281203A (en) * | 1979-06-01 | 1981-07-28 | Shell Oil Company | (Cyclopropyl)vinyl alkyl ether derivatives |
| US4409398A (en) * | 1981-08-13 | 1983-10-11 | Shell Oil Company | Preparation of (1R, cis)-oxyimino-substituted cyclo-propanecarboxylic acids |
| FR2517677B1 (fr) * | 1981-12-09 | 1986-05-16 | Roussel Uclaf | Nouveaux ethers dont les restes organiques comportent des atomes chiraux, leur procede de preparation et leur application au dedoublement des alcools ou de certains composes de structure hemiacetalique. |
-
1984
- 1984-07-28 IN IN537/CAL/84A patent/IN162785B/en unknown
- 1984-09-28 GB GB848424561A patent/GB8424561D0/en active Pending
-
1985
- 1985-09-26 US US06/780,651 patent/US4680418A/en not_active Expired - Fee Related
- 1985-09-27 DE DE8585306901T patent/DE3565264D1/de not_active Expired
- 1985-09-27 EP EP85306901A patent/EP0180325B1/en not_active Expired
- 1985-09-27 JP JP60214414A patent/JPS6272681A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4680418A (en) | 1987-07-14 |
| EP0180325B1 (en) | 1988-09-28 |
| EP0180325A1 (en) | 1986-05-07 |
| GB8424561D0 (en) | 1984-11-07 |
| DE3565264D1 (en) | 1988-11-03 |
| IN162785B (en, 2012) | 1988-07-09 |
| JPH0574590B2 (en, 2012) | 1993-10-18 |
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