GB1309331A - Process for preparing methyl and ethyl-10-epoxy-7-preparing methyl and ethyl-10-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoate - Google Patents
Process for preparing methyl and ethyl-10-epoxy-7-preparing methyl and ethyl-10-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoateInfo
- Publication number
- GB1309331A GB1309331A GB70270A GB70270A GB1309331A GB 1309331 A GB1309331 A GB 1309331A GB 70270 A GB70270 A GB 70270A GB 70270 A GB70270 A GB 70270A GB 1309331 A GB1309331 A GB 1309331A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- methyl
- give
- epoxy
- dimethyl
- 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.)
- Expired
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 ethyl magnesium halide Chemical class 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- PPJVXZVTPWQOQS-UHFFFAOYSA-N 1-ethoxy-1-(1-ethoxyethoxy)ethane Chemical compound CCOC(C)OC(C)OCC PPJVXZVTPWQOQS-UHFFFAOYSA-N 0.000 abstract 1
- QRDYHKLLQVGVNO-UHFFFAOYSA-N 2-(3-iodopropyl)-2-methyl-1,3-dioxolane Chemical compound ICCCC1(C)OCCO1 QRDYHKLLQVGVNO-UHFFFAOYSA-N 0.000 abstract 1
- HFYAEUXHCMTPOL-UHFFFAOYSA-N 3-Methyl-1-penten-3-ol Chemical compound CCC(C)(O)C=C HFYAEUXHCMTPOL-UHFFFAOYSA-N 0.000 abstract 1
- XVRIEWDDMODMGA-UHFFFAOYSA-N 5-chloropentan-2-one Chemical compound CC(=O)CCCCl XVRIEWDDMODMGA-UHFFFAOYSA-N 0.000 abstract 1
- RZXWNQYIRHMNTQ-UHFFFAOYSA-N 5-iodopentan-2-one Chemical compound CC(=O)CCCI RZXWNQYIRHMNTQ-UHFFFAOYSA-N 0.000 abstract 1
- TYNZTYZVNLOLDZ-UHFFFAOYSA-N 5-methylhept-4-enal Chemical compound CC(=CCCC=O)CC TYNZTYZVNLOLDZ-UHFFFAOYSA-N 0.000 abstract 1
- ATJNRJIDXLMSJP-UHFFFAOYSA-N 6-ethyl-10-methyldodeca-5,9-dien-2-one Chemical compound CCC(C)=CCCC(CC)=CCCC(C)=O ATJNRJIDXLMSJP-UHFFFAOYSA-N 0.000 abstract 1
- YVNCFSXFUCUCOE-UHFFFAOYSA-N 7-methylnon-6-en-3-ol Chemical compound CCC(O)CCC=C(C)CC YVNCFSXFUCUCOE-UHFFFAOYSA-N 0.000 abstract 1
- HKOJBOJXQMRVFD-UHFFFAOYSA-N 7-methylnon-6-en-3-one Chemical compound CCC(C)=CCCC(=O)CC HKOJBOJXQMRVFD-UHFFFAOYSA-N 0.000 abstract 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 1
- 241000238631 Hexapoda Species 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 abstract 1
- CTSAXXHOGZNKJR-UHFFFAOYSA-N methyl 2-diethoxyphosphorylacetate Chemical compound CCOP(=O)(OCC)CC(=O)OC CTSAXXHOGZNKJR-UHFFFAOYSA-N 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000012439 solid excipient Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- 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
-
- 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
- C07C45/511—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 involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—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 involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1309331 Preparation of 10-epoxy-7-ethyl-3, 11-dimethyl-2,6-tridecadienoate J A FINDLAY 6 Jan 1970 [6 Jan 1969] 702/70 Headings C2C and C2P Methyl or ethyl 10-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoate where R represents methyl or ethyl is prepared by reacting 3-methyl-1-penten-3-ol with ethyl vinyl ether in the presence of a catalyst to give α-ethoxyethyl ether, which is heated with a catalyst to give 5-methyl-4-hepten-1-al, which is reacted with ethyl magnesium halide to give 7-methyl-6-nonen-3-ol, which is oxidized to 7- methyl-6-nonen-3-one, which is treated with the ylid from 4-oxopentyl-1-triphenylphosphonium iodide ethylene ketal to give 6-ethyl- 10-methyldodeca-5,9-dien-2-one which is treated with the anion from a dialkylcarbomethoxymethyl or dialkylcarboethoxymethyl phosphonate to give the methyl or ethyl 3,11-dimethyl-7- ethyl-tri-deca-2,6,10-trienoate which is treated with a N-halosuccinimide in dimethoxyethane and water and then with an alkali metal isopropoxide. The compounds may be used with a carrier in the control of insect populations. The carriers may be solvents, aqueous emulsions, or solid excipients to form dusting powders. 4 - Oxopentyl - 1 - triphenylphosphonium iodide ethylene ketal is prepared from 5-chloro-2- pentanone by converting to 5-iodo-2-pentanone, treating with ethylene glycol to obtain 5-iodo- 2-pentanone ethylene ketal and then treating with triphenyl phosphine. Diethylcarbomethoxymethyl phosphonate is prepared by reacting methyl chloroacetate and triethyl phosphite followed by distillation. Ethyl chloroacetate may be used to prepare the corresponding ethoxy compound. Reference has been directed by the Comptroller to Specifications 1,209,190 and 1,209,903.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA039,394,A CA951322A (en) | 1969-01-06 | 1969-01-06 | Process for preparing methyl and ethyl 10-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1309331A true GB1309331A (en) | 1973-03-07 |
Family
ID=4084779
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB70270A Expired GB1309331A (en) | 1969-01-06 | 1970-01-06 | Process for preparing methyl and ethyl-10-epoxy-7-preparing methyl and ethyl-10-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoate |
| GB4001172A Expired GB1309332A (en) | 1969-01-06 | 1970-01-06 | Substituted pentenes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4001172A Expired GB1309332A (en) | 1969-01-06 | 1970-01-06 | Substituted pentenes |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS494206B1 (en) |
| CA (1) | CA951322A (en) |
| CH (1) | CH521335A (en) |
| DE (1) | DE2000274A1 (en) |
| FR (1) | FR2030126A1 (en) |
| GB (2) | GB1309331A (en) |
| IT (1) | IT1047882B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1673092A (en) * | 1991-04-23 | 1992-11-17 | Nippon Suisan Kaisha, Ltd. | Process for producing epoxy derivative |
| BE1019331A5 (en) | 2010-05-10 | 2012-06-05 | Flooring Ind Ltd Sarl | FLOOR PANEL AND METHODS FOR MANUFACTURING FLOOR PANELS. |
-
1969
- 1969-01-06 CA CA039,394,A patent/CA951322A/en not_active Expired
- 1969-12-22 IT IT26170/69A patent/IT1047882B/en active
- 1969-12-30 CH CH1946869A patent/CH521335A/en not_active IP Right Cessation
-
1970
- 1970-01-05 DE DE19702000274 patent/DE2000274A1/en active Pending
- 1970-01-06 GB GB70270A patent/GB1309331A/en not_active Expired
- 1970-01-06 GB GB4001172A patent/GB1309332A/en not_active Expired
- 1970-01-06 FR FR7000303A patent/FR2030126A1/fr not_active Withdrawn
- 1970-01-06 JP JP45002267A patent/JPS494206B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1309332A (en) | 1973-03-07 |
| DE2000274A1 (en) | 1970-07-16 |
| CH521335A (en) | 1972-04-15 |
| FR2030126A1 (en) | 1970-10-30 |
| CA951322A (en) | 1974-07-16 |
| IT1047882B (en) | 1980-10-20 |
| JPS494206B1 (en) | 1974-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |