CH633767A5 - Process for the preparation of the novel 6-oxo-2-methylhepta-2,4-dienoic acid and its derivatives - Google Patents
Process for the preparation of the novel 6-oxo-2-methylhepta-2,4-dienoic acid and its derivatives Download PDFInfo
- Publication number
- CH633767A5 CH633767A5 CH1387977A CH1387977A CH633767A5 CH 633767 A5 CH633767 A5 CH 633767A5 CH 1387977 A CH1387977 A CH 1387977A CH 1387977 A CH1387977 A CH 1387977A CH 633767 A5 CH633767 A5 CH 633767A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- hepta
- dienoic acid
- parts
- oxo
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 13
- JGBAVQBLUTYORM-UHFFFAOYSA-N 2-methyl-6-oxohepta-2,4-dienoic acid Chemical compound CC(=O)C=CC=C(C)C(O)=O JGBAVQBLUTYORM-UHFFFAOYSA-N 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- -1 hydrocarbon radical Chemical class 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000002329 infrared spectrum Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000002211 ultraviolet spectrum Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- VMILCVCSESPPIA-UHFFFAOYSA-N ethyl 2-methyl-6-oxohepta-2,4-dienoate Chemical compound CCOC(=O)C(C)=CC=CC(C)=O VMILCVCSESPPIA-UHFFFAOYSA-N 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 230000002140 halogenating effect Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003495 polar organic solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WVBSKESCGVGQLY-UHFFFAOYSA-N (1,5-dimethyl-6-oxocyclohexa-2,4-dien-1-yl) acetate Chemical compound CC(=O)OC1(C)C=CC=C(C)C1=O WVBSKESCGVGQLY-UHFFFAOYSA-N 0.000 description 4
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 4
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 4
- CYQURDQINYLLRQ-UHFFFAOYSA-N 6-acetyloxy-2-methylhepta-3,5-dienoic acid Chemical compound OC(=O)C(C)C=CC=C(C)OC(C)=O CYQURDQINYLLRQ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000021466 carotenoid Nutrition 0.000 description 4
- 150000001747 carotenoids Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- YGLFMNCKXCUZIB-UHFFFAOYSA-N ethyl 6-acetyloxy-2-methylhepta-3,5-dienoate Chemical compound CCOC(=O)C(C)C=CC=C(C)OC(C)=O YGLFMNCKXCUZIB-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ZVSILIQCTOABFX-UHFFFAOYSA-N methyl 6-acetyloxy-2-methylhepta-3,5-dienoate Chemical compound COC(=O)C(C)C=CC=C(C)OC(C)=O ZVSILIQCTOABFX-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- HRCPVGJZALMPSW-UHFFFAOYSA-N ethyl 3-bromo-2-methyl-6-oxohept-4-enoate Chemical compound CCOC(=O)C(C)C(Br)C=CC(C)=O HRCPVGJZALMPSW-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 235000002864 food coloring agent Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- JHCXOJFLDRHXCP-UHFFFAOYSA-N methyl 2-methyl-6-oxohepta-2,4-dienoate Chemical compound COC(=O)C(C)=CC=CC(C)=O JHCXOJFLDRHXCP-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 1,2-dimethoxyethane;hydrate Chemical compound O.COCCOC ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 0.000 description 1
- GJNCXCPHNRATIQ-UHFFFAOYSA-N 1-bromoazepan-2-one Chemical compound BrN1CCCCCC1=O GJNCXCPHNRATIQ-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- KSKXSFZGARKWOW-UHFFFAOYSA-N 6-methylhepta-3,5-dien-2-one Chemical compound CC(C)=CC=CC(C)=O KSKXSFZGARKWOW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- PEZJGEVXNLBIGZ-UHFFFAOYSA-N CC(=O)C=CC=C(C)C(=O)NC1=CC=CC=C1 Chemical compound CC(=O)C=CC=C(C)C(=O)NC1=CC=CC=C1 PEZJGEVXNLBIGZ-UHFFFAOYSA-N 0.000 description 1
- BQBGNOHINCQAKP-UHFFFAOYSA-N CC(C=CC=C(C)OC(=O)C)C(=O)NC1=CC=CC=C1 Chemical compound CC(C=CC=C(C)OC(=O)C)C(=O)NC1=CC=CC=C1 BQBGNOHINCQAKP-UHFFFAOYSA-N 0.000 description 1
- BHUJAMRTVHCTNK-UHFFFAOYSA-N COCCOC.C(C)NCC Chemical compound COCCOC.C(C)NCC BHUJAMRTVHCTNK-UHFFFAOYSA-N 0.000 description 1
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- CBAKQTZQORWDTM-UHFFFAOYSA-N N,N,2-trimethyl-6-oxohepta-2,4-dienamide Chemical compound CN(C(C(=CC=CC(C)=O)C)=O)C CBAKQTZQORWDTM-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- NDUJGCWCEQYCRZ-UHFFFAOYSA-N [7-(cyclohexylamino)-6-methyl-7-oxohepta-2,4-dien-2-yl] acetate Chemical compound CC(=O)OC(C)=CC=CC(C)C(=O)NC1CCCCC1 NDUJGCWCEQYCRZ-UHFFFAOYSA-N 0.000 description 1
- AFFHKEGNSCTOHU-UHFFFAOYSA-N [7-(diethylamino)-6-methyl-7-oxohepta-2,4-dien-2-yl] acetate Chemical compound CCN(CC)C(=O)C(C)C=CC=C(C)OC(C)=O AFFHKEGNSCTOHU-UHFFFAOYSA-N 0.000 description 1
- JLESQZYEZHAQJG-UHFFFAOYSA-N [7-(dimethylamino)-6-methyl-7-oxohepta-2,4-dien-2-yl] acetate Chemical compound CN(C(C(C=CC=C(C)OC(C)=O)C)=O)C JLESQZYEZHAQJG-UHFFFAOYSA-N 0.000 description 1
- 238000006137 acetoxylation reaction Methods 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- GEJFGEWCXXJZEC-UHFFFAOYSA-N benzyl 2-methyl-6-oxohepta-2,4-dienoate Chemical compound C(C1=CC=CC=C1)OC(C(=CC=CC(C)=O)C)=O GEJFGEWCXXJZEC-UHFFFAOYSA-N 0.000 description 1
- GFJPNAYYWNARKY-UHFFFAOYSA-N benzyl 6-acetyloxy-2-methylhepta-3,5-dienoate Chemical compound C(C1=CC=CC=C1)OC(C(C=CC=C(C)OC(C)=O)C)=O GFJPNAYYWNARKY-UHFFFAOYSA-N 0.000 description 1
- MJKDMTNFGJEWNN-UHFFFAOYSA-N butyl 6-acetyloxy-2-methylhepta-3,5-dienoate Chemical compound C(CCC)OC(C(C=CC=C(C)OC(C)=O)C)=O MJKDMTNFGJEWNN-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000005293 duran Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000989 food dye Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GCYDJSKTCBITBG-UHFFFAOYSA-N methyl hepta-2,4-dienoate Chemical compound CCC=CC=CC(=O)OC GCYDJSKTCBITBG-UHFFFAOYSA-N 0.000 description 1
- NSBNSZAXNUGWDJ-UHFFFAOYSA-O monopyridin-1-ium tribromide Chemical compound Br[Br-]Br.C1=CC=[NH+]C=C1 NSBNSZAXNUGWDJ-UHFFFAOYSA-O 0.000 description 1
- LRKPTZSELINOSY-UHFFFAOYSA-N n,n-diethyl-2-methyl-6-oxohepta-2,4-dienamide Chemical compound CCN(CC)C(=O)C(C)=CC=CC(C)=O LRKPTZSELINOSY-UHFFFAOYSA-N 0.000 description 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- YODZWDHUGVOQJW-UHFFFAOYSA-N propyl 6-acetyloxy-2-methylhepta-3,5-dienoate Chemical compound C(CC)OC(C(C=CC=C(C)OC(C)=O)C)=O YODZWDHUGVOQJW-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762652356 DE2652356A1 (de) | 1976-11-17 | 1976-11-17 | 6-oxo-2-methyl-hepta-2,4-diensaeure, deren ester und amide sowie ein verfahren zur herstellung der neuen verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH633767A5 true CH633767A5 (en) | 1982-12-31 |
Family
ID=5993370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1387977A CH633767A5 (en) | 1976-11-17 | 1977-11-14 | Process for the preparation of the novel 6-oxo-2-methylhepta-2,4-dienoic acid and its derivatives |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH633767A5 (enExample) |
| DE (1) | DE2652356A1 (enExample) |
| FR (1) | FR2371419A1 (enExample) |
| GB (1) | GB1590033A (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2165962A (en) * | 1936-10-29 | 1939-07-11 | Ig Farbenindustrie Ag | Production of alkylidene diethers or ether-esters |
| CH601100A5 (enExample) * | 1974-08-05 | 1978-06-30 | Hoffmann La Roche |
-
1976
- 1976-11-17 DE DE19762652356 patent/DE2652356A1/de not_active Withdrawn
-
1977
- 1977-11-08 FR FR7733549A patent/FR2371419A1/fr active Granted
- 1977-11-14 CH CH1387977A patent/CH633767A5/de not_active IP Right Cessation
- 1977-11-16 GB GB4764277A patent/GB1590033A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2371419A1 (fr) | 1978-06-16 |
| DE2652356A1 (de) | 1978-05-18 |
| FR2371419B1 (enExample) | 1983-10-14 |
| GB1590033A (en) | 1981-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH629736A5 (en) | Process for preparing 2-phenylethanol derivatives | |
| CH494730A (de) | Verfahren zur Herstellung von Dibenzocyclopentenen | |
| EP0004621B1 (de) | Verfahren zur mehrstufigen Synthese von Zeaxanthin und Alloxanthin über Cyclohexanon- und Cyclohexanolderivate; Cyclohexanon- und Cyclohexanolderivate | |
| DE2432235C2 (de) | Verfahren zur Herstellung von Lavandulol, seinen Estern und von 3,5,5-Trimethyl-hepta-1,6-dien-3-ol | |
| CH636073A5 (en) | Process for the preparation of substituted cyclopropanecarboxylates | |
| DE102014003489A1 (de) | (Z,Z,E,)1-Chlor-6,10,12-pentadecdecatrienund Verfahren zur Herstellung von (Z,Z,E)-7, 11, 13-Hexadecatrienal unter Verwendung desselben | |
| DE2753454A1 (de) | Quadratsaeureester | |
| DE69410318T2 (de) | Verfahren zur Herstellung eines Chinonderivates und Zwischenprodukt bei dessen Herstellung | |
| DE68913236T2 (de) | Verfahren für die Herstellung halogenierter Sulfone. | |
| CH633767A5 (en) | Process for the preparation of the novel 6-oxo-2-methylhepta-2,4-dienoic acid and its derivatives | |
| DE10112067A1 (de) | Verfahren zur Herstellung von 2,7-Dimethyl-2,4,6-octarienal-monoacetalen | |
| EP0346852B1 (de) | Verfahren zur Herstellung von 4-chlor-3-alkoxy-but-2E-en-säurealkylester | |
| EP0006180B1 (de) | 3-Phenoxybenzylidenamine und 3-Benzylbenzylidenamine, ein Verfahren zu deren Herstellung sowie deren Verwendung zur Herstellung der entsprechenden Aldehyde | |
| EP0075237B1 (de) | Verfahren zur Herstellung von Derivaten des 1-Formyl-2,6,6-trimethyl-cyclohex-1-ens | |
| EP0061669B1 (de) | Verbessertes Verfahren zur Herstellung von Cyclohexan-1,3-dionen sowie einige neue bicyclische Cyclohexan-1,3-dione | |
| DE2814347A1 (de) | Verfahren zur herstellung von steroidsaeuren | |
| DE4239945C2 (de) | 14 alpha, 15 alpha-Methylensteroide und Verfahren zu ihrer Herstellung | |
| DE2547223C3 (de) | Verfahren zur Herstellung von 2,6,6-Trimethyl-cyclohex-2-en-1 -on | |
| EP0103749B1 (de) | Dialkoxymethyl-butyrolactone, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung | |
| EP0394644A2 (de) | Halogenbenzolderivate | |
| EP0025939A1 (de) | Aliphatische Methoxy- und Hydroxynitrile, deren Herstellung und deren Verwendung als Riechstoff | |
| DE1543995C (de) | Verfahren zur Herstellung von 5 (3 see AminoalkyhdenH0,11 dihydro 5H dibenzo eckige Klammer auf a,d ecki ge Klammer zu cycloheptenen | |
| EP0673945A1 (de) | Herstellung eines Wittigestersalzes | |
| AT368758B (de) | Verfahren zum abbau der carboxylgruppe von 3-oxo -pregna-4-en-20-carbonsaeure (delta4-bnc) bzw. 3-oxo-pregna-1,4-dien-20-carbonsaeure (delta1,4-bnc) | |
| DE1815788A1 (de) | 4,5-substituierte N-Oxy- und Hydroxyhydoimidazole |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |