DE3142114A1 - Verfahren zur herstellung von dodec-11-en-1-ylderivaten - Google Patents
Verfahren zur herstellung von dodec-11-en-1-ylderivatenInfo
- Publication number
- DE3142114A1 DE3142114A1 DE19813142114 DE3142114A DE3142114A1 DE 3142114 A1 DE3142114 A1 DE 3142114A1 DE 19813142114 DE19813142114 DE 19813142114 DE 3142114 A DE3142114 A DE 3142114A DE 3142114 A1 DE3142114 A1 DE 3142114A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- dodec
- acid
- stands
- derivative
- 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.)
- Withdrawn
Links
- -1 dodec-11-en-1-yl Chemical class 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 125000005907 alkyl ester group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- KNRCBASNXNXUQQ-UHFFFAOYSA-N 11-hydroxyundecanoic acid Chemical compound OCCCCCCCCCCC(O)=O KNRCBASNXNXUQQ-UHFFFAOYSA-N 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 229910014033 C-OH Inorganic materials 0.000 claims description 4
- 229910014570 C—OH Inorganic materials 0.000 claims description 4
- 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
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- 150000004681 metal hydrides Chemical class 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 3
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000021736 acetylation Effects 0.000 claims description 2
- 238000006640 acetylation reaction Methods 0.000 claims description 2
- 150000001298 alcohols Chemical class 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
- 230000003197 catalytic effect Effects 0.000 claims description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 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 8
- 239000012429 reaction media Substances 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- QNXYZQSFDTZEBK-UHFFFAOYSA-N dodec-11-en-1-ol Chemical compound OCCCCCCCCCCC=C QNXYZQSFDTZEBK-UHFFFAOYSA-N 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000003016 pheromone Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- DIGWSCGMTNOSDZ-UHFFFAOYSA-N tetradec-13-enoic acid Chemical compound OC(=O)CCCCCCCCCCCC=C DIGWSCGMTNOSDZ-UHFFFAOYSA-N 0.000 description 3
- IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- VASIFKMMXNGAGN-UHFFFAOYSA-N methyl 11-hydroxyundecanoate Chemical compound COC(=O)CCCCCCCCCCO VASIFKMMXNGAGN-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 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
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FRYAHUIXVSJEBC-UHFFFAOYSA-N 11-hydroxyundecyl acetate Chemical compound CC(=O)OCCCCCCCCCCCO FRYAHUIXVSJEBC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 241000060469 Eupoecilia ambiguella Species 0.000 description 1
- YYFLOYVXFFHZAY-UHFFFAOYSA-L O[Cr](O)(=O)=O.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.Cl Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.Cl YYFLOYVXFFHZAY-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000005667 attractant Substances 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
- 239000011230 binding agent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- XRXDLBRJHUCCHH-UHFFFAOYSA-N diiodomethane Chemical compound ICI.ICI XRXDLBRJHUCCHH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N icos-13-enoic acid Chemical compound CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004920 integrated pest control Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000005949 ozonolysis reaction Methods 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
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001568 sexual effect Effects 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method 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)
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 |
|---|---|
| DE3142114A1 true DE3142114A1 (de) | 1982-06-16 |
Family
ID=10960083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813142114 Withdrawn DE3142114A1 (de) | 1980-10-24 | 1981-10-23 | Verfahren zur herstellung von dodec-11-en-1-ylderivaten |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE890748A (pt) |
| DE (1) | DE3142114A1 (pt) |
| ES (1) | ES506524A0 (pt) |
| FR (1) | FR2492816A1 (pt) |
| GB (1) | GB2085881A (pt) |
| GR (1) | GR74694B (pt) |
| HU (1) | HU180386B (pt) |
| IT (1) | IT1139272B (pt) |
| PT (1) | PT73870B (pt) |
| RO (1) | RO82277A (pt) |
| YU (1) | YU252981A (pt) |
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 |
| US9695385B2 (en) | 2013-03-13 | 2017-07-04 | Stepan Company | Surfactants based on monounsaturated fatty alcohol derivatives |
| BR112018009885B1 (pt) * | 2015-11-18 | 2021-09-21 | Provivi, Inc | Métodos de síntese de derivado de olefina graxo através de metátese de olefina |
| JP7153937B2 (ja) | 2017-02-17 | 2022-10-17 | プロビビ インコーポレイテッド | オレフィンメタセシスによるフェロモンおよび関連材料の合成方法 |
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 YU YU02529/81A patent/YU252981A/xx unknown
- 1981-10-23 FR FR8119930A patent/FR2492816A1/fr active Pending
- 1981-10-23 ES ES506524A patent/ES506524A0/es active Granted
- 1981-10-23 GB GB8132023A patent/GB2085881A/en not_active Withdrawn
- 1981-10-23 PT PT73870A patent/PT73870B/pt unknown
- 1981-10-23 DE DE19813142114 patent/DE3142114A1/de not_active Withdrawn
- 1981-10-23 GR GR66339A patent/GR74694B/el unknown
- 1981-11-19 RO RO81105823A patent/RO82277A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT73870A (en) | 1981-11-01 |
| ES8206411A1 (es) | 1982-08-16 |
| GB2085881A (en) | 1982-05-06 |
| IT1139272B (it) | 1986-09-24 |
| RO82277B (ro) | 1983-08-30 |
| PT73870B (en) | 1983-01-25 |
| YU252981A (en) | 1983-10-31 |
| FR2492816A1 (fr) | 1982-04-30 |
| BE890748A (fr) | 1982-04-16 |
| IT8124627A0 (it) | 1981-10-22 |
| RO82277A (ro) | 1983-09-26 |
| GR74694B (pt) | 1984-07-04 |
| ES506524A0 (es) | 1982-08-16 |
| HU180386B (en) | 1983-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0633258B1 (de) | Verbessertes Verfahren zur Herstellung von Astaxanthin, neue Zwischenprodukte hierfür sowie ein Verfahren zu deren Herstellung | |
| Wissner et al. | Reaction of tert-butyldimethylsilyl esters with oxalyl chloride-dimethylformamide: preparation of carboxylic acid chlorides under neutral conditions | |
| DE2653838C2 (pt) | ||
| CH651292A5 (de) | Bicyclo(3,3,0)octan-derivate. | |
| EP0031932A2 (de) | Substituierte Lactone, Pentacarbonsäurederivate und Verfahren zu ihrer Herstellung | |
| DE3142114A1 (de) | Verfahren zur herstellung von dodec-11-en-1-ylderivaten | |
| DE3817399A1 (de) | Verfahren zur herstellung von e7/z9-alkadien-1-olen und deren an der hydroxylgruppe geschuetzten derivaten | |
| EP0075680B1 (de) | Substituierte Furanone sowie Verfahren zur Herstellung von 3,4-Dihydro-alpha-pyronen und substituierten Furanonen | |
| EP0112502B1 (de) | Omega,omega-Diacyloxy-2,6-dimethyl-octatriensäureester und -aldehyde, Verfahren zu ihrer Herstellung und Verwendung zur Synthese von Terpenverbindungen | |
| DD281191A5 (de) | Verfahren zur herstellung von 17alpha-ethinyl-17beta-hydroxy-18-mehtyl-4,15-estradien-3-on | |
| EP0676388B1 (de) | Verfahren zur Herstellung von substituierten Phenylessigsäurederivaten und neue Zwischenprodukte | |
| DE2212589C3 (de) | Verfahren zur Herstellung von 13 beta-R-4,9,11-gonatrienen und 13 beta-R-4,5-seco-9,l 1-gonadiene als Z wise henproduk te | |
| DE2653604C2 (pt) | ||
| EP0008077B1 (de) | Neue Prostaglandinderivate in der Delta-2-PGF2 und Delta-2-PGE2-Reihe, Verfahren zu deren Herstellung und ihre Verwendung als Arzneimittel | |
| EP0103749B1 (de) | Dialkoxymethyl-butyrolactone, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung | |
| DE3424328A1 (de) | Verfahren zur herstellung von 3,11-di-(methyl)-nonakosan-2-on sowie 2,10-di-(methyl)-octakosansaeurealkylester und verfahren zur herstellung der letzteren | |
| EP0059307A1 (de) | Verfahren zur Herstellung von 2-Oxabicyclo(3.3.0)octanderivaten und danach erhältliche Produkte | |
| EP0446925B1 (de) | Verfahren zur Herstellung von beta-Resorcylsäurederivaten | |
| DE3046059C2 (de) | 4-Halogen-5,5-dialkoxypentansäureester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von 2,2-Dialkyl-3-formylcyclopropancarbonsäureestern | |
| AT358059B (de) | Verfahren zur herstellung von neuen oxiranen | |
| DE10063410B4 (de) | Verfahren zur Herstellung von optisch aktiven Enonen von Cyclopentan und Zwischenprodukte dafür | |
| DE2952068A1 (de) | Substituierte lactone und verfahren zu deren herstellung | |
| EP0855395A1 (de) | Verfahren für die Herstellung von Oxetan-2-onen und Zwischenprodukte | |
| DE2830971A1 (de) | Dihydrobisabolene und dihydrobisabolol, deren herstellung und verwendung als duftstoffe | |
| EP0251050A2 (de) | Neue 2,4,4-Trimethyl-cyclohex-2-en-1-on-derivate und deren Verwendung als Riechstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |