JPS6064942A - ３，１１‐ジメチル‐２‐ノナコサノンの製造方法 - Google Patents
３，１１‐ジメチル‐２‐ノナコサノンの製造方法Info
- Publication number
- JPS6064942A JPS6064942A JP59133484A JP13348484A JPS6064942A JP S6064942 A JPS6064942 A JP S6064942A JP 59133484 A JP59133484 A JP 59133484A JP 13348484 A JP13348484 A JP 13348484A JP S6064942 A JPS6064942 A JP S6064942A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- methyl
- formula
- solution
- reacted
- 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
- GQJLFAGGBJJGDA-UHFFFAOYSA-N (3R,11R)-3,11-Dimethyl-2-nonacosanone Natural products CCCCCCCCCCCCCCCCCCC(C)CCCCCCCC(C)C(C)=O GQJLFAGGBJJGDA-UHFFFAOYSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 2 , 10-dimethyloctacosanoic acid ester Chemical class 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 229910000761 Aluminium amalgam Inorganic materials 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- KVWLUDFGXDFFON-UHFFFAOYSA-N lithium;methanidyl(trimethyl)silane Chemical compound [Li+].C[Si](C)(C)[CH2-] KVWLUDFGXDFFON-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 239000000203 mixture Substances 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000003016 pheromone Substances 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229960002703 undecylenic acid Drugs 0.000 description 5
- 241000238657 Blattella germanica Species 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 230000008029 eradication Effects 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229910052705 radium Inorganic materials 0.000 description 4
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XTWJVMPEOYBUME-UHFFFAOYSA-N 2-methylundec-10-enoic acid Chemical compound OC(=O)C(C)CCCCCCCC=C XTWJVMPEOYBUME-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- UNZVCQADHJCNDL-UHFFFAOYSA-M octadecyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCCCCCCCCCC)C1=CC=CC=C1 UNZVCQADHJCNDL-UHFFFAOYSA-M 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QITHFSMOCKLNPT-UHFFFAOYSA-N 10-methyloctacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(C)CCCCCCCCC(O)=O QITHFSMOCKLNPT-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- UGKKOFVRPCHOHR-UHFFFAOYSA-J [Cu](Cl)(Cl)(Cl)Cl.[Li].[Li] Chemical compound [Cu](Cl)(Cl)(Cl)Cl.[Li].[Li] UGKKOFVRPCHOHR-UHFFFAOYSA-J 0.000 description 2
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 150000002940 palladium Chemical class 0.000 description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- UMSRUHQFWJHBHT-ZETCQYMHSA-N (3R)-6-bromo-3-methylhex-1-ene Chemical compound C[C@H](CCCBr)C=C UMSRUHQFWJHBHT-ZETCQYMHSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- OTELGGYNGCBJGP-UHFFFAOYSA-N 11-oxododecanoic acid Natural products CC(=O)CCCCCCCCCC(O)=O OTELGGYNGCBJGP-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- AYMLNRRLOWTSPF-UHFFFAOYSA-N 2,10-dimethyloctacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(C)CCCCCCCC(C)C(O)=O AYMLNRRLOWTSPF-UHFFFAOYSA-N 0.000 description 1
- PXSBSBDNZRLRLK-UHFFFAOYSA-N 2-(2h-pyran-2-yloxy)-2h-pyran Chemical compound O1C=CC=CC1OC1OC=CC=C1 PXSBSBDNZRLRLK-UHFFFAOYSA-N 0.000 description 1
- LXBPIEXIBORHQI-UHFFFAOYSA-N 2-(8-methylhexacosoxy)oxane Chemical compound O1C(CCCC1)OCCCCCCCC(CCCCCCCCCCCCCCCCCC)C LXBPIEXIBORHQI-UHFFFAOYSA-N 0.000 description 1
- GLCIPJOIEVLTPR-UHFFFAOYSA-N 2-chlorohexane Chemical compound CCCCC(C)Cl GLCIPJOIEVLTPR-UHFFFAOYSA-N 0.000 description 1
- UXDPXVCCHHJHFP-UHFFFAOYSA-N 2-methyl-10-oxoundecanoic acid Chemical compound OC(=O)C(C)CCCCCCCC(C)=O UXDPXVCCHHJHFP-UHFFFAOYSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VBATUBQIYXCZPA-UHFFFAOYSA-N 3-methylpent-1-en-4-yn-3-ol Chemical compound C=CC(O)(C)C#C VBATUBQIYXCZPA-UHFFFAOYSA-N 0.000 description 1
- KUSQMNUGEQARFL-UHFFFAOYSA-N 5-chloro-3-methylpent-3-en-1-yne Chemical compound C#CC(C)=CCCl KUSQMNUGEQARFL-UHFFFAOYSA-N 0.000 description 1
- UAZVFQCIRVFQTO-UHFFFAOYSA-N 6-methyltetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(C)CCCCC(O)=O UAZVFQCIRVFQTO-UHFFFAOYSA-N 0.000 description 1
- GKROSDUSGBVCAM-UHFFFAOYSA-N 7-methylpentacosan-1-ol Chemical compound CC(CCCCCCO)CCCCCCCCCCCCCCCCCC GKROSDUSGBVCAM-UHFFFAOYSA-N 0.000 description 1
- WBAHRGLUIZRAAI-UHFFFAOYSA-N 8-methylhexacosan-1-ol Chemical compound CC(CCCCCCCO)CCCCCCCCCCCCCCCCCC WBAHRGLUIZRAAI-UHFFFAOYSA-N 0.000 description 1
- KNPGTJGXMGNBAY-UHFFFAOYSA-N 8-oxo-nonanoic acid Chemical compound CC(=O)CCCCCCC(O)=O KNPGTJGXMGNBAY-UHFFFAOYSA-N 0.000 description 1
- UKHMENMPHVRROO-UHFFFAOYSA-N 9-acetyl pelargonic acid Chemical compound CC(=O)CCCCCCCCC(O)=O UKHMENMPHVRROO-UHFFFAOYSA-N 0.000 description 1
- KDQADQYAIVDJNP-UHFFFAOYSA-N 9-bromononan-2-one Chemical compound CC(=O)CCCCCCCBr KDQADQYAIVDJNP-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- ANRLLHWZOKNCOL-UHFFFAOYSA-N CC(CCCCCCCCCCCCCCCCCC)=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CC(CCCCCCCCCCCCCCCCCC)=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 ANRLLHWZOKNCOL-UHFFFAOYSA-N 0.000 description 1
- FLBDWWUDQSTNCW-UHFFFAOYSA-M CCCCCCCCCCCCCCCCCC[Mg]Br Chemical compound CCCCCCCCCCCCCCCCCC[Mg]Br FLBDWWUDQSTNCW-UHFFFAOYSA-M 0.000 description 1
- 102100024479 Cell division cycle-associated protein 3 Human genes 0.000 description 1
- SZZYLYUVTJLJQM-UHFFFAOYSA-J Cl[Cu](Cl)(Cl)Cl Chemical compound Cl[Cu](Cl)(Cl)Cl SZZYLYUVTJLJQM-UHFFFAOYSA-J 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 101000980907 Homo sapiens Cell division cycle-associated protein 3 Proteins 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 238000006550 Oxy-Cope rearrangement reaction Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BRGJPAUDJAJJLL-UHFFFAOYSA-N S-phenyl nonadecanethioate Chemical compound C(CCCCCCCCCCCCCCCCCC)(SC1=CC=CC=C1)=O BRGJPAUDJAJJLL-UHFFFAOYSA-N 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241000718541 Tetragastris balsamifera Species 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SUQHGDPPUZCCAF-UHFFFAOYSA-L [Ra+2].CC([O-])=O.CC([O-])=O Chemical compound [Ra+2].CC([O-])=O.CC([O-])=O SUQHGDPPUZCCAF-UHFFFAOYSA-L 0.000 description 1
- 150000001241 acetals Chemical group 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- KAKJZWSUVDRWQU-UHFFFAOYSA-N butan-2-yl but-2-enoate Chemical compound CCC(C)OC(=O)C=CC KAKJZWSUVDRWQU-UHFFFAOYSA-N 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
- OOCUOKHIVGWCTJ-UHFFFAOYSA-N chloromethyl(trimethyl)silane Chemical compound C[Si](C)(C)CCl OOCUOKHIVGWCTJ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000009193 crawling Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- FNENWZWNOPCZGK-UHFFFAOYSA-N ethyl 2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(C)=O FNENWZWNOPCZGK-UHFFFAOYSA-N 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- DXBULVYHTICWKT-UHFFFAOYSA-N ethyl 6-bromohexanoate Chemical compound CCOC(=O)CCCCCBr DXBULVYHTICWKT-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 231100000944 irritant response Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- PZPGYOWJZWYSMX-UHFFFAOYSA-N methyl 10-methyloctacos-10-enoate Chemical compound CCCCCCCCCCCCCCCCCC=C(C)CCCCCCCCC(=O)OC PZPGYOWJZWYSMX-UHFFFAOYSA-N 0.000 description 1
- BRFCTNGBHIIBKK-UHFFFAOYSA-N methyl 10-methyloctacosanoate Chemical compound CCCCCCCCCCCCCCCCCCC(C)CCCCCCCCC(=O)OC BRFCTNGBHIIBKK-UHFFFAOYSA-N 0.000 description 1
- IUXGBIGUMXTVHV-UHFFFAOYSA-N methyl 2,10-dimethyloctacosanoate Chemical compound CCCCCCCCCCCCCCCCCCC(C)CCCCCCCC(C)C(=O)OC IUXGBIGUMXTVHV-UHFFFAOYSA-N 0.000 description 1
- TVAMIPDEZYHWDZ-UHFFFAOYSA-N methyl 2-methyl-10-oxoundecanoate Chemical compound COC(=O)C(C)CCCCCCCC(C)=O TVAMIPDEZYHWDZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- SJFUDWKNZGXSLV-UHFFFAOYSA-N octan-2-yl acetate Chemical compound CCCCCCC(C)OC(C)=O SJFUDWKNZGXSLV-UHFFFAOYSA-N 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RWRDJVNMSZYMDV-UHFFFAOYSA-L radium chloride Chemical compound [Cl-].[Cl-].[Ra+2] RWRDJVNMSZYMDV-UHFFFAOYSA-L 0.000 description 1
- 229910001630 radium chloride Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000002602 strong irritant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/673—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 isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU832388A HU193494B (en) | 1983-07-01 | 1983-07-01 | Process for production of 3,11-dimethil-2-nonakozanon |
| HU2251-2388/83 | 1983-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6064942A true JPS6064942A (ja) | 1985-04-13 |
Family
ID=10959101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59133484A Pending JPS6064942A (ja) | 1983-07-01 | 1984-06-29 | ３，１１‐ジメチル‐２‐ノナコサノンの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS6064942A (it) |
| DD (1) | DD218614A5 (it) |
| DE (1) | DE3424328A1 (it) |
| FR (1) | FR2549042B1 (it) |
| GB (1) | GB2142632B (it) |
| HU (1) | HU193494B (it) |
| IT (1) | IT1176376B (it) |
| PL (2) | PL248479A1 (it) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01117140A (ja) * | 1987-10-30 | 1989-05-10 | Sharp Corp | 給紙装置 |
| JP2008174387A (ja) * | 2007-01-22 | 2008-07-31 | Xerox Corp | 多数シート挿入機トレイのための整列ゲート |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7316501B2 (en) | 2004-05-20 | 2008-01-08 | Christian Thoma | Apparatus and method for mixing dissimilar fluids |
| GB0822091D0 (en) | 2008-12-03 | 2009-01-07 | Givaudan Sa | Organic compounds |
-
1983
- 1983-07-01 HU HU832388A patent/HU193494B/hu not_active IP Right Cessation
-
1984
- 1984-06-29 FR FR8410308A patent/FR2549042B1/fr not_active Expired
- 1984-06-29 PL PL24847984A patent/PL248479A1/xx unknown
- 1984-06-29 GB GB08416629A patent/GB2142632B/en not_active Expired
- 1984-06-29 DD DD84264733A patent/DD218614A5/de unknown
- 1984-06-29 IT IT21695/84A patent/IT1176376B/it active
- 1984-06-29 JP JP59133484A patent/JPS6064942A/ja active Pending
- 1984-06-29 PL PL25337584A patent/PL253375A1/xx unknown
- 1984-07-02 DE DE19843424328 patent/DE3424328A1/de not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01117140A (ja) * | 1987-10-30 | 1989-05-10 | Sharp Corp | 給紙装置 |
| JP2008174387A (ja) * | 2007-01-22 | 2008-07-31 | Xerox Corp | 多数シート挿入機トレイのための整列ゲート |
Also Published As
| Publication number | Publication date |
|---|---|
| PL248479A1 (en) | 1985-09-24 |
| DD218614A5 (de) | 1985-02-13 |
| PL253375A1 (en) | 1986-02-25 |
| IT1176376B (it) | 1987-08-18 |
| GB2142632A (en) | 1985-01-23 |
| DE3424328A1 (de) | 1985-01-03 |
| FR2549042A1 (fr) | 1985-01-18 |
| GB8416629D0 (en) | 1984-08-01 |
| FR2549042B1 (fr) | 1987-03-06 |
| IT8421695A0 (it) | 1984-06-29 |
| HU193494B (en) | 1987-10-28 |
| IT8421695A1 (it) | 1985-12-29 |
| HUT35625A (en) | 1985-07-29 |
| GB2142632B (en) | 1986-11-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kowalski et al. | Enone mesylates. Precursors to. beta.-substituted cyclohexenones | |
| JP2618220B2 (ja) | 殺虫剤製造用中間体の製造方法 | |
| US4198532A (en) | Novel alcohol odorants | |
| US3919329A (en) | Synthesis of the pink bollworm sex pheromone | |
| Naoshima et al. | Synthesis of (Z)-7-eicosen-11-one and (Z)-7-nonadecen-11-one, the sex pheromone of peach fruit moth | |
| EP0054065B1 (en) | Ambrinol and its homologues | |
| US4212830A (en) | Process for preparing insect pheromones | |
| GB2142632A (en) | Process for the preparation of the pheromone 3,11-dimethyl-2-nonacosanone | |
| US4083855A (en) | Method for producing a γ-lactone | |
| US3783141A (en) | 3,7,9,11-tetramethyl-10-alkoxy or benzyloxytrideca - 2,7,11 - trienoic acids and esters containing a 4 position triple or double bond | |
| JPS5850209B2 (ja) | ２ ２− ジメチル−３−（２ ２−ジハロビニル）−シクロプロパンカルボンサンユウドウタイノ セイゾウホウ | |
| US3728396A (en) | Aliphatic ketones | |
| US3749744A (en) | Oxo-substituted alpha,beta-unsaturated alkylated fatty acids and esters | |
| US4181683A (en) | 1,7-Octadien-3-one and process for preparing the same | |
| US3706804A (en) | Quaternary alkyl aliphatic ketones | |
| FR2478084A1 (fr) | Nouveaux esters de l'acide tricyclo(5.2.1.02,6)decane-2-carboxylique, leurs procedes de preparation et leur utilisation en parfumerie | |
| US3803187A (en) | 2-chloro-substituted unsaturated esters useful for the control of insects | |
| US3887596A (en) | 2-Oxo substituted unsaturated esters useful for the control of insects | |
| US3801611A (en) | Oxy-substituted 3,4-allenic fatty acid esters | |
| JPS647978B2 (it) | ||
| JP2771866B2 (ja) | 不飽和テルペン類の製造方法 | |
| JPH03501384A (ja) | アルキルテトラメチルシクロヘキサン誘導体及び香料としてのそれらの使用 | |
| CA1224485A (fr) | PROCEDE DE PREPARATION DE COMPOSES HALOGENES EN .alpha. D'UN GROUPEMENT ELECTROATTRACTEUR | |
| US2849491A (en) | 6, 8-dimethyl-5-nonen-2-one | |
| US3887592A (en) | 2-Hydroxy or acetoxy substituted esters useful for the control of insects |