HU180386B - Process for producing 11-dodecen-1-ol and 11-dodecen-1-yl-acetate of insect-feromone activity - Google Patents
Process for producing 11-dodecen-1-ol and 11-dodecen-1-yl-acetate of insect-feromone activity Download PDFInfo
- Publication number
- HU180386B HU180386B HU80802575A HU257580A HU180386B HU 180386 B HU180386 B HU 180386B HU 80802575 A HU80802575 A HU 80802575A HU 257580 A HU257580 A HU 257580A HU 180386 B HU180386 B HU 180386B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- ester
- acid
- dodecen
- defined above
- Prior art date
Links
- QNXYZQSFDTZEBK-UHFFFAOYSA-N dodec-11-en-1-ol Chemical compound OCCCCCCCCCCC=C QNXYZQSFDTZEBK-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 14
- ANBOMSJGDBBKMR-UHFFFAOYSA-N 11-Dodecenyl acetate Chemical compound CC(=O)OCCCCCCCCCCC=C ANBOMSJGDBBKMR-UHFFFAOYSA-N 0.000 title description 4
- 230000000694 effects Effects 0.000 title description 2
- 150000002148 esters Chemical class 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 230000000397 acetylating effect Effects 0.000 claims abstract description 4
- 230000003647 oxidation Effects 0.000 claims abstract description 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- -1 11-dodecen-1-yl Chemical class 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 11
- KNRCBASNXNXUQQ-UHFFFAOYSA-N 11-hydroxyundecanoic acid Chemical compound OCCCCCCCCCCC(O)=O KNRCBASNXNXUQQ-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 8
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 claims description 7
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
- 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 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 230000021736 acetylation Effects 0.000 claims description 3
- 238000006640 acetylation reaction Methods 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000032050 esterification Effects 0.000 abstract description 2
- 238000005886 esterification reaction Methods 0.000 abstract description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003016 pheromone Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 description 2
- ZGPVCRPNBPLGDV-UHFFFAOYSA-N 11-oxoundecanoic acid Chemical compound OC(=O)CCCCCCCCCC=O ZGPVCRPNBPLGDV-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- RHGDHBUHYHTCSH-UHFFFAOYSA-N methyl 11-oxoundecanoate Chemical compound COC(=O)CCCCCCCCCC=O RHGDHBUHYHTCSH-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FRYAHUIXVSJEBC-UHFFFAOYSA-N 11-hydroxyundecyl acetate Chemical compound CC(=O)OCCCCCCCCCCCO FRYAHUIXVSJEBC-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000060469 Eupoecilia ambiguella Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000000877 Sex Attractant Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- ICQJNCNVUCTBHZ-UHFFFAOYSA-N dec-1-en-1-ol Chemical compound CCCCCCCCC=CO ICQJNCNVUCTBHZ-UHFFFAOYSA-N 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004920 integrated pest control Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011656 manganese carbonate Substances 0.000 description 1
- 235000006748 manganese carbonate Nutrition 0.000 description 1
- 229940093474 manganese carbonate Drugs 0.000 description 1
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU80802575A HU180386B (en) | 1980-10-24 | 1980-10-24 | Process for producing 11-dodecen-1-ol and 11-dodecen-1-yl-acetate of insect-feromone activity |
| BE1/10334A BE890748A (fr) | 1980-10-24 | 1981-10-16 | Procede de preparation de derives de 11-dedecen-1-yle |
| IT24627/81A IT1139272B (it) | 1980-10-24 | 1981-10-22 | Procedimento per la preparazione di derivati dell' 11-dodecen-1-ile |
| GR66339A GR74694B (fr) | 1980-10-24 | 1981-10-23 | |
| ES506524A ES506524A0 (es) | 1980-10-24 | 1981-10-23 | Procedimiento de preparacion de derivados 11-dodecen-1-ilos |
| YU02529/81A YU252981A (en) | 1980-10-24 | 1981-10-23 | Process for obtaining 11-dodecene-1-yl derivatives |
| GB8132023A GB2085881A (en) | 1980-10-24 | 1981-10-23 | A process for the preparation of 11-dodecen-1-ol and derivatives |
| FR8119930A FR2492816A1 (fr) | 1980-10-24 | 1981-10-23 | Procede de preparation de derives de 11-dodecen-1-yle |
| DE19813142114 DE3142114A1 (de) | 1980-10-24 | 1981-10-23 | Verfahren zur herstellung von dodec-11-en-1-ylderivaten |
| PT73870A PT73870B (en) | 1980-10-24 | 1981-10-23 | Process for the preparation of 11-dodecen-1-yl derivatives |
| RO81105823A RO82277A (fr) | 1980-10-24 | 1981-11-19 | Procede pour la preparation des derives de 11-dodecen-1-yl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU80802575A HU180386B (en) | 1980-10-24 | 1980-10-24 | Process for producing 11-dodecen-1-ol and 11-dodecen-1-yl-acetate of insect-feromone activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180386B true HU180386B (en) | 1983-02-28 |
Family
ID=10960083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80802575A HU180386B (en) | 1980-10-24 | 1980-10-24 | Process for producing 11-dodecen-1-ol and 11-dodecen-1-yl-acetate of insect-feromone activity |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE890748A (fr) |
| DE (1) | DE3142114A1 (fr) |
| ES (1) | ES506524A0 (fr) |
| FR (1) | FR2492816A1 (fr) |
| GB (1) | GB2085881A (fr) |
| GR (1) | GR74694B (fr) |
| HU (1) | HU180386B (fr) |
| IT (1) | IT1139272B (fr) |
| PT (1) | PT73870B (fr) |
| RO (1) | RO82277A (fr) |
| YU (1) | YU252981A (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4560792A (en) * | 1982-07-20 | 1985-12-24 | Phillips Petroleum Company | Disproportionation of functional olefins |
| DE3815044A1 (de) * | 1988-05-04 | 1989-11-16 | Basf Ag | 1-tert.-butoxy-(omega)-alkene und deren verwendung als riechstoffe |
| EP2967033B1 (fr) | 2013-03-13 | 2019-10-02 | Stepan Company | Tensioactifs a base de dérives alcool gras mono-insaturés |
| WO2017087710A2 (fr) * | 2015-11-18 | 2017-05-26 | Provivi, Inc. | Production de dérivés d'oléfines gras par l'intermédiaire d'une métathèse d'oléfines |
| CN110603240B (zh) | 2017-02-17 | 2022-11-15 | 普罗维维公司 | 通过烯烃复分解合成信息素和相关物质 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1096345B (de) * | 1959-02-28 | 1961-01-05 | Bayer Ag | Verfahren zur Herstellung von Hexadecadien-(10, 12)-ol-(1) |
| CA961862A (en) * | 1971-04-23 | 1975-01-28 | Andre Comeau | Trans-8-trans-10-dodecadien-1-o1 |
-
1980
- 1980-10-24 HU HU80802575A patent/HU180386B/hu unknown
-
1981
- 1981-10-16 BE BE1/10334A patent/BE890748A/fr not_active IP Right Cessation
- 1981-10-22 IT IT24627/81A patent/IT1139272B/it active
- 1981-10-23 ES ES506524A patent/ES506524A0/es active Granted
- 1981-10-23 YU YU02529/81A patent/YU252981A/xx unknown
- 1981-10-23 PT PT73870A patent/PT73870B/pt unknown
- 1981-10-23 FR FR8119930A patent/FR2492816A1/fr active Pending
- 1981-10-23 GR GR66339A patent/GR74694B/el unknown
- 1981-10-23 DE DE19813142114 patent/DE3142114A1/de not_active Withdrawn
- 1981-10-23 GB GB8132023A patent/GB2085881A/en not_active Withdrawn
- 1981-11-19 RO RO81105823A patent/RO82277A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8206411A1 (es) | 1982-08-16 |
| FR2492816A1 (fr) | 1982-04-30 |
| PT73870B (en) | 1983-01-25 |
| ES506524A0 (es) | 1982-08-16 |
| PT73870A (en) | 1981-11-01 |
| RO82277B (ro) | 1983-08-30 |
| IT1139272B (it) | 1986-09-24 |
| BE890748A (fr) | 1982-04-16 |
| DE3142114A1 (de) | 1982-06-16 |
| IT8124627A0 (it) | 1981-10-22 |
| GR74694B (fr) | 1984-07-04 |
| RO82277A (fr) | 1983-09-26 |
| YU252981A (en) | 1983-10-31 |
| GB2085881A (en) | 1982-05-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5334740A (en) | Cyclohexanetriol derivatives | |
| US4571428A (en) | 6-Substituted-4-hydroxy-tetrahydropyran-2-ones | |
| HU180386B (en) | Process for producing 11-dodecen-1-ol and 11-dodecen-1-yl-acetate of insect-feromone activity | |
| SU1277897A3 (ru) | Способ получени 1,1-диоксо-6-бром(или-6,6-дибром)пеницилланоилоксиметиловых эфиров 6-(2-азидо-2-фенилацетамидо)пенициллановой кислоты | |
| US4276216A (en) | Synthesis of dioxabicyclo[3.2.1]octanes and oxepanes | |
| Tsukamoto et al. | Preparation and reaction of difluorinated malonaldehydic acid derivatives: a new route to functionalized α, α-difluorinated esters and amides | |
| IRIE et al. | Synthesis of the Methyl Ester of AK-Toxin II, a Host-Specific Toxin to Japanese white Pear, and Its Congeners:: Structure-Toxicity Relationship of the Toxin | |
| US4258205A (en) | 2,2-Dimethylcyclopropanecarbaldehyde dimethyl acetal derivatives | |
| EP0116375B1 (fr) | Acide (1RS, 4SR, 5RS)-4-(5-hydroxy-4,8-diméthyl-8-nonen-1-yl)-4-méthyl-3,8-dioxabicyclo(3.2.1.)octane-1-acétique et procédé pour sa préparation | |
| US4603213A (en) | Total synthesis of 1RS,4SR,5RS-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid | |
| US3749744A (en) | Oxo-substituted alpha,beta-unsaturated alkylated fatty acids and esters | |
| SU1533625A3 (ru) | Способ получени (+)-(3S, 4R)-3,4,7,11-тетраметил-6,10-додекадиенал | |
| KR850000227B1 (ko) | 옥소옥세판 유도체의 합성방법 | |
| US4201874A (en) | 3-Isopropenyl-6-heptenoic acid | |
| JP2856838B2 (ja) | ステロイド誘導体の製造方法 | |
| US20110301370A1 (en) | Method for preparing oreganic acid | |
| EP0580476B1 (fr) | Procédé de fabrication de 6E-leucotriène B4 et produits intermédiaires dudit procédé de fabrication | |
| US4169860A (en) | Insect pheromone | |
| RU2429220C1 (ru) | Способ получения 11(е)-тетрадецен-1-илацетата | |
| US4841071A (en) | 6-substituted-4-hydroxy-tetrahydropyran-2-ones | |
| SU767083A1 (ru) | Способ получени 1,2,5,5,9-пентаметил3-кето- -октагидронафталена | |
| US5196608A (en) | Use of an allylchloride for preparing an aldehyde | |
| JP3249847B2 (ja) | Ｚ−シクロヘキシリデン酢酸誘導体の製造方法 | |
| SU648100A3 (ru) | Способ получени замещенных или незамещенных производных 3-тиофурана | |
| JPH0517914B2 (fr) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |