DE1543804A1 - 3-Furylmethylalkohole - Google Patents
3-FurylmethylalkoholeInfo
- Publication number
- DE1543804A1 DE1543804A1 DE19661543804 DE1543804A DE1543804A1 DE 1543804 A1 DE1543804 A1 DE 1543804A1 DE 19661543804 DE19661543804 DE 19661543804 DE 1543804 A DE1543804 A DE 1543804A DE 1543804 A1 DE1543804 A1 DE 1543804A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- acid
- ester
- benzyl
- furylmethyl
- 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.)
- Pending
Links
- -1 3-furylmethyl alcohols Chemical class 0.000 title claims description 35
- 239000002253 acid Substances 0.000 claims description 21
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- JOOXCMJARBKPKM-UHFFFAOYSA-N laevulinic acid Natural products CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- GBFQMYZCARWIAY-UHFFFAOYSA-N 5-benzylfuran-3-carboxylic acid Chemical compound OC(=O)C1=COC(CC=2C=CC=CC=2)=C1 GBFQMYZCARWIAY-UHFFFAOYSA-N 0.000 claims description 2
- 238000003512 Claisen condensation reaction Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- DGEHQARARXBTFY-UHFFFAOYSA-N methyl 5-benzylfuran-3-carboxylate Chemical compound COC(=O)C1=COC(CC=2C=CC=CC=2)=C1 DGEHQARARXBTFY-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000004718 beta keto acids Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 150000002085 enols Chemical group 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- XEMLEMIOCGLVMR-UHFFFAOYSA-N ethyl 5-benzylfuran-3-carboxylate Chemical compound CCOC(=O)C1=COC(CC=2C=CC=CC=2)=C1 XEMLEMIOCGLVMR-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229940040102 levulinic acid Drugs 0.000 description 2
- ZKHQSQYLKSSYIP-UHFFFAOYSA-N methyl furan-3-carboxylate Chemical compound COC(=O)C=1C=COC=1 ZKHQSQYLKSSYIP-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005909 ethyl alcohol group Chemical group 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MKTBDDIZMVUFDS-UHFFFAOYSA-N methyl 5-(chloromethyl)furan-3-carboxylate Chemical compound COC(=O)C1=COC(CCl)=C1 MKTBDDIZMVUFDS-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- BUBOVHRAKJTFKI-UHFFFAOYSA-M sodium;4-hydroxy-2,4-dioxobutanoate Chemical compound [Na+].OC(=O)C(=O)CC([O-])=O BUBOVHRAKJTFKI-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000010792 warming 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3778866A GB1168798A (en) | 1965-12-09 | 1965-12-09 | Furan Derivatives and a Process for Their Preparation. |
| GB52406/65A GB1168797A (en) | 1965-12-09 | 1965-12-09 | Cyclopropane Carboxylic Acid Derivatives and their use as Insecticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543804A1 true DE1543804A1 (de) | 1970-01-02 |
Family
ID=26263575
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543805 Granted DE1543805B1 (de) | 1965-12-09 | 1966-12-08 | Substituierte 3-Furylmethylester und Verfahren zu deren Herstellung sowie deren Verwendung als Insekticide |
| DE1793559A Expired DE1793559C3 (de) | 1965-12-09 | 1966-12-08 | Verfahren zur Herstellung von Furan 3 carbonsaureestern Ausscheidung aus 1543804 |
| DE19661543804 Pending DE1543804A1 (de) | 1965-12-09 | 1966-12-08 | 3-Furylmethylalkohole |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543805 Granted DE1543805B1 (de) | 1965-12-09 | 1966-12-08 | Substituierte 3-Furylmethylester und Verfahren zu deren Herstellung sowie deren Verwendung als Insekticide |
| DE1793559A Expired DE1793559C3 (de) | 1965-12-09 | 1966-12-08 | Verfahren zur Herstellung von Furan 3 carbonsaureestern Ausscheidung aus 1543804 |
Country Status (15)
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992526A (en) * | 1966-06-28 | 1976-11-16 | Dainippon Jochugiku Kabushiki Kaisha | 5-Ethoxymethyl furfuryl ester of chrysanthemumic acid and its use as an insecticide |
| US3982013A (en) * | 1966-06-28 | 1976-09-21 | Dainippon Jochugiku Kabushiki Kaisha | 5-Phenylvinylfurfurylester of chrysanthemumic acid |
| US3932470A (en) * | 1966-06-28 | 1976-01-13 | Dainippon Jochugiku Kabushiki Kaisha | Substituted furfurylesters of chrysantheumumic acid |
| US3968238A (en) * | 1966-06-28 | 1976-07-06 | Dainippon Jochugiku Kabushiki Kaisha | 5-Acetyl furfurylester of chrysanthemumic acid |
| US3832467A (en) * | 1967-08-11 | 1974-08-27 | Sumitomo Chemical Co | Insecticidal chrysanthemate compositions and their method of use |
| US3669989A (en) * | 1968-06-13 | 1972-06-13 | Sumitomo Chemical Co | Cyclopropanecarboxylic acid esters |
| DE2005489C3 (de) * | 1969-02-07 | 1982-04-15 | Roussel-Uclaf, 75007 Paris | cis-3,3-Dimethyl-2S-(2'-R↓1↓-2'-R↓2↓-vinyl)-cyclopropan-1R-carbonsäure-5"-benzyl-3"-furylmethylester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende insektizide Mittel |
| US3857858A (en) * | 1969-04-08 | 1974-12-31 | Sumitomo Chemical Co | Cyclopropane carboxylic acid esters |
| FR2045177A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-06-13 | 1971-02-26 | Roussel Uclaf | |
| FR2077677B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-02-04 | 1973-05-25 | Roussel Uclaf | |
| US3835220A (en) * | 1970-03-19 | 1974-09-10 | Sumitomo Chemical Co | Insecticidal composition comprising vinylcyclopropanecarboxylates |
| US3716560A (en) * | 1970-03-26 | 1973-02-13 | Sumitomo Chemical Co | 4,5-tetramethylene furfuryl and 4,5-tetramethylene-3-furylmethyl chrysanthemates |
| JPS4821487B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-08-04 | 1973-06-29 | ||
| US3755368A (en) * | 1971-03-01 | 1973-08-28 | Penick S & Co | Formylation of carboxylic compounds with carbon monoxide |
| US3873716A (en) * | 1971-03-01 | 1975-03-25 | Procter & Gamble | Insecticidal esters of chrysanthemic acid and alcohols related to 3-hydroxymethylbenzofuran |
| US4622337A (en) * | 1972-05-25 | 1986-11-11 | National Research Development Corporation | 2,2-dimethyl-3-(2-halovinyl)cyclopropane carboxlic acid ester pesticides |
| GB1410080A (en) * | 1972-12-21 | 1975-10-15 | Nat Res Dev | Oxime derivatives of 2,2-dimethyl-3-formyl cyclopropane carboxylic acid and their use as insecticides |
| US3994882A (en) * | 1974-07-22 | 1976-11-30 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Nitrofuran derivatives, process for the preparation thereof and compositions containing same as active ingredient |
| FI53971C (fi) * | 1974-08-15 | 1978-09-11 | Kemira Oy | Foerfarande foer framstaellning av estrar av furfuryalkohol eller dess derivat med laegre alifatiska karbonsyror |
| US4220591A (en) * | 1975-11-26 | 1980-09-02 | Commonwealth Scientific And Industrial Research Organization | Insecticidal esters |
| FR2341307A1 (fr) * | 1976-02-19 | 1977-09-16 | Roussel Uclaf | Pyrethrinoides a titre de medicaments et compositions pharmaceutiques les renfermant |
| LU75478A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-07-28 | 1978-02-08 | ||
| SE446527B (sv) * | 1976-09-21 | 1986-09-22 | Roussel Uclaf | Nya cyklopropankarboxylsyraestrar med en polyhalogenerad substituent, sett for framstellning derav samt anvendning derav i pesticidkompositioner |
| FR2364884A1 (fr) * | 1976-09-21 | 1978-04-14 | Roussel Uclaf | Nouveaux esters d'acides cyclopropane, carboxyliques comportant un substituant polyhalogene, procedes de preparation et compositions insecticides les renfermant |
| US4234582A (en) * | 1978-05-10 | 1980-11-18 | Chugai Seiyaku Kabushiki Kaisha | Trialkyl isocyanates used as pesticides |
| FR2426673A1 (fr) * | 1978-05-25 | 1979-12-21 | Nat Res Dev | Pesticides du type pyrethrine |
| US4356023A (en) * | 1980-06-30 | 1982-10-26 | Shell Oil Company | Certain herbicidal tetrahydrofurans |
| US4676977A (en) * | 1982-06-28 | 1987-06-30 | Roussel Uclaf | Stabilized pesticidal emulsions |
| US4677117A (en) * | 1982-06-28 | 1987-06-30 | Roussel Uclaf | Stabilized pesticidal compositions |
| US4477679A (en) * | 1983-03-01 | 1984-10-16 | Cpc International Inc. | Production of alkyl-5-substituted-3-furoate compounds |
| DE3546371A1 (de) * | 1985-12-31 | 1987-07-02 | Basf Ag | Pyrethroide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen sowie vorprodukte fuer die herstellung der pyrethroide |
| DE10007411A1 (de) | 2000-02-18 | 2001-08-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| AR029677A1 (es) | 2000-06-29 | 2003-07-10 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas y acaricidas |
| DE102004001271A1 (de) | 2004-01-08 | 2005-08-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| ES2387927T3 (es) * | 2004-12-17 | 2012-10-04 | Devgen Nv | Composiciones nematicidas |
| JP5066843B2 (ja) * | 2006-06-15 | 2012-11-07 | 住友化学株式会社 | エステル化合物及びその有害生物防除用途 |
| DE102006046688B3 (de) * | 2006-09-29 | 2008-01-24 | Siemens Ag | Kälteanlage mit einem warmen und einem kalten Verbindungselement und einem mit den Verbindungselementen verbundenen Wärmerohr |
| DE102007045953B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| MX2011009918A (es) | 2009-03-25 | 2011-10-06 | Bayer Cropscience Ag | Combinaciones de principios activos propiedades insecticidas y acaricidas. |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| CN103058897A (zh) * | 2012-12-27 | 2013-04-24 | 苏州大学 | 一种手性β-羟基磺酰胺的制备方法 |
| DE102014107739B4 (de) | 2014-06-02 | 2023-12-07 | Jacques Tchouangueu | Moskitonetz mit Insektenfalle |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2470349A (en) * | 1945-05-29 | 1949-05-17 | California Spray Chemical Corp | Cyclopropyl furyl propenone |
| US2891889A (en) * | 1953-11-20 | 1959-06-23 | Union Carbide Corp | Insecticidal compositions containing cyclethrin |
| US3101296A (en) * | 1959-11-09 | 1963-08-20 | Harvel Res Corp | Synergistic insecticidal composition |
| NL296103A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-08-06 | |||
| BE660565A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-03-18 |
-
1965
- 1965-12-09 GB GB52406/65A patent/GB1168797A/en not_active Expired
-
1966
- 1966-11-21 IL IL26910A patent/IL26910A/en unknown
- 1966-11-21 IL IL30842A patent/IL30842A/xx unknown
- 1966-11-23 DK DK604566AA patent/DK128607B/da not_active IP Right Cessation
- 1966-11-28 SE SE16271/68A patent/SE353719B/xx unknown
- 1966-11-28 SE SE16272/68A patent/SE353906B/xx unknown
- 1966-11-28 SE SE16259/66A patent/SE325582B/xx unknown
- 1966-12-02 CA CA976,970A patent/CA1030152A/en not_active Expired
- 1966-12-05 FR FR86170A patent/FR1503260A/fr not_active Expired
- 1966-12-05 US US598901A patent/US3466304A/en not_active Expired - Lifetime
- 1966-12-05 US US598923A patent/US3465007A/en not_active Expired - Lifetime
- 1966-12-06 NL NL6617119A patent/NL6617119A/xx unknown
- 1966-12-06 NO NO165885A patent/NO118155B/no unknown
- 1966-12-08 CH CH1654768A patent/CH507931A/fr not_active IP Right Cessation
- 1966-12-08 DE DE19661543805 patent/DE1543805B1/de active Granted
- 1966-12-08 DE DE1793559A patent/DE1793559C3/de not_active Expired
- 1966-12-08 CH CH1748866A patent/CH513587A/fr not_active IP Right Cessation
- 1966-12-08 CH CH1120171A patent/CH524593A/fr not_active IP Right Cessation
- 1966-12-08 DE DE19661543804 patent/DE1543804A1/de active Pending
- 1966-12-09 AT AT1138366A patent/AT275238B/de active
- 1966-12-09 AT AT10130/68A patent/AT285590B/de not_active IP Right Cessation
- 1966-12-09 AT AT05936/68A patent/AT279599B/de not_active IP Right Cessation
- 1966-12-09 BE BE690984D patent/BE690984A/xx not_active IP Right Cessation
- 1966-12-09 OA OA52688A patent/OA02187A/xx unknown
- 1966-12-09 ES ES334365A patent/ES334365A1/es not_active Expired
-
1968
- 1968-10-16 DK DK497368AA patent/DK136035B/da not_active IP Right Cessation
- 1968-10-16 DK DK497468A patent/DK136036C/da not_active IP Right Cessation
-
1969
- 1969-03-14 US US807406A patent/US3542928A/en not_active Expired - Lifetime
- 1969-11-20 NL NL6917481A patent/NL6917481A/xx unknown
- 1969-11-20 NL NL6917482A patent/NL6917482A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |