CN1348434A - 用卡罗尔反应制备γ,δ－不饱和酮 - Google Patents
用卡罗尔反应制备γ,δ－不饱和酮 Download PDFInfo
- Publication number
- CN1348434A CN1348434A CN99812906A CN99812906A CN1348434A CN 1348434 A CN1348434 A CN 1348434A CN 99812906 A CN99812906 A CN 99812906A CN 99812906 A CN99812906 A CN 99812906A CN 1348434 A CN1348434 A CN 1348434A
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- China
- Prior art keywords
- general formula
- methyl
- reaction
- alcohol
- karol
- Prior art date
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- Pending
Links
- 150000002576 ketones Chemical class 0.000 title claims abstract description 15
- 238000006563 Carroll rearrangement reaction Methods 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 34
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 7
- -1 methoxyl group Chemical group 0.000 claims description 43
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 21
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 19
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 19
- 229930007744 linalool Natural products 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 claims description 12
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 claims description 12
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000457 gamma-lactone group Chemical group 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- IUDWWFNDSJRYRV-UHFFFAOYSA-N 3,7-dimethyloct-1-en-3-ol Chemical compound CC(C)CCCC(C)(O)C=C IUDWWFNDSJRYRV-UHFFFAOYSA-N 0.000 claims 1
- CCCXGQLQJHWTLZ-UHFFFAOYSA-N geranyl linalool Natural products CC(=CCCC(=CCCCC(C)(O)CCC=C(C)C)C)C CCCXGQLQJHWTLZ-UHFFFAOYSA-N 0.000 claims 1
- IQDXAJNQKSIPGB-HQSZAHFGSA-N geranyllinalool Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)(O)C=C IQDXAJNQKSIPGB-HQSZAHFGSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 abstract description 36
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 25
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 description 29
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 230000008569 process Effects 0.000 description 10
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 8
- DJAHKBBSJCDSOZ-AJLBTXRUSA-N (5z,9e,13e)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one;(5e,9e,13e)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CCC(C)=O.CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CCC(C)=O DJAHKBBSJCDSOZ-AJLBTXRUSA-N 0.000 description 7
- 229940009827 aluminum acetate Drugs 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 229950006156 teprenone Drugs 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 5
- LTUMRKDLVGQMJU-IUBLYSDUSA-N farnesyl acetone Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)=O LTUMRKDLVGQMJU-IUBLYSDUSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- LTUMRKDLVGQMJU-UHFFFAOYSA-N famesylacetone Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=O LTUMRKDLVGQMJU-UHFFFAOYSA-N 0.000 description 4
- HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical compound CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 description 4
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 description 4
- XHYJMHUBEDCSPT-UHFFFAOYSA-N C(C)(=O)O.C(C)(=O)[Al](C(C)=O)C(C)=O Chemical compound C(C)(=O)O.C(C)(=O)[Al](C(C)=O)C(C)=O XHYJMHUBEDCSPT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003509 tertiary alcohols Chemical class 0.000 description 3
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical group CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 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
- PVGHQBCTMALNFO-UHFFFAOYSA-N 2-acetyl-3-oxobutanoic acid Chemical compound CC(=O)C(C(C)=O)C(O)=O PVGHQBCTMALNFO-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JRTBBCBDKSRRCY-UHFFFAOYSA-N 3,7-dimethyloct-6-en-3-ol Chemical compound CCC(C)(O)CCC=C(C)C JRTBBCBDKSRRCY-UHFFFAOYSA-N 0.000 description 1
- XHRGPLDMNNGHCX-UHFFFAOYSA-N 3-Methylbutyl 3-oxobutanoate Chemical compound CC(C)CCOC(=O)CC(C)=O XHRGPLDMNNGHCX-UHFFFAOYSA-N 0.000 description 1
- ALZLTHLQMAFAPA-UHFFFAOYSA-N 3-Methylbutyrolactone Chemical compound CC1COC(=O)C1 ALZLTHLQMAFAPA-UHFFFAOYSA-N 0.000 description 1
- BDCLDNALSPBWPQ-UHFFFAOYSA-N 3-oxohexanoic acid Chemical compound CCCC(=O)CC(O)=O BDCLDNALSPBWPQ-UHFFFAOYSA-N 0.000 description 1
- 240000007185 Albizia julibrissin Species 0.000 description 1
- 235000011468 Albizia julibrissin Nutrition 0.000 description 1
- 101150114104 CROT gene Proteins 0.000 description 1
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 241000921313 Phyllopodium Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 1
- UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical compound CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 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
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001399 aluminium compounds Chemical class 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000004718 beta keto acids Chemical class 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BAWIJQDONYVQRF-UHFFFAOYSA-N geranylfarnesylacetone Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=O BAWIJQDONYVQRF-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- JPTOCTSNXXKSSN-UHFFFAOYSA-N methylheptenone Chemical compound CCCC=CC(=O)CC JPTOCTSNXXKSSN-UHFFFAOYSA-N 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000002899 organoaluminium compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011949 solid catalyst Substances 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
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 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
-
- 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
- C07C45/676—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 by elimination of carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19840746.7 | 1998-09-07 | ||
| DE19840746A DE19840746A1 (de) | 1998-09-07 | 1998-09-07 | Verfahren zur Herstellung gamma,delta-ungesättigter Ketone durch Carroll-Reaktion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1348434A true CN1348434A (zh) | 2002-05-08 |
Family
ID=7880056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99812906A Pending CN1348434A (zh) | 1998-09-07 | 1999-09-02 | 用卡罗尔反应制备γ,δ－不饱和酮 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1112245A1 (id) |
| JP (1) | JP2002524435A (id) |
| KR (1) | KR20010074970A (id) |
| CN (1) | CN1348434A (id) |
| AU (1) | AU5858399A (id) |
| CA (1) | CA2343521A1 (id) |
| DE (1) | DE19840746A1 (id) |
| ID (1) | ID27392A (id) |
| IL (1) | IL141689A0 (id) |
| WO (1) | WO2000014046A1 (id) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102050714A (zh) * | 2010-12-08 | 2011-05-11 | 成都自豪药业有限公司 | 一种合成替普瑞酮的方法 |
| CN103058839A (zh) * | 2013-01-25 | 2013-04-24 | 四川源基制药有限公司 | 替普瑞酮合成及纯化工艺 |
| CN104326890A (zh) * | 2014-11-21 | 2015-02-04 | 山东新和成药业有限公司 | 一种Carroll反应连续化工艺方法 |
| CN104513117A (zh) * | 2013-10-08 | 2015-04-15 | 中国科学院大连化学物理研究所 | 一种手性β-乙炔基酮化合物的催化不对称合成方法 |
| CN116212943A (zh) * | 2022-12-05 | 2023-06-06 | 江苏宏邦化工科技有限公司 | 一种新型碱性催化剂的制备方法及其在制备甲基庚烯酮中的应用 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002121166A (ja) * | 2000-10-16 | 2002-04-23 | Kuraray Co Ltd | 不飽和ケトンの製造方法 |
| JP2002121165A (ja) * | 2000-10-16 | 2002-04-23 | Kuraray Co Ltd | 不飽和ケトンの製造方法 |
| WO2008047690A1 (en) * | 2006-10-11 | 2008-04-24 | Eisai R & D Management Co., Ltd. | Process for preparing geranylgeranylacetone |
| CN106946673A (zh) | 2015-12-11 | 2017-07-14 | 帝斯曼知识产权资产管理有限公司 | 制造6,10,14‑三甲基十五烷‑2‑酮的方法 |
| WO2018108606A1 (en) | 2016-12-12 | 2018-06-21 | Dsm Ip Assets B.V. | Process for the manufacture of 6,10-dimethylundecan-2-one, isophytol, alpha-tocopherol (acetate) and further intermediates thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH493453A (de) * | 1968-07-23 | 1970-07-15 | Basf Ag | Verfahren zur Herstellung von 6,10-Dimethyl-undecatrien-(3,5,10)-on-(2) |
| DE2928944A1 (de) * | 1979-07-18 | 1981-02-12 | Basf Ag | Verbessertes verfahren zur herstellung von hoeheren ungesaettigten ketonen |
| DE19647117A1 (de) * | 1996-11-14 | 1998-05-28 | Basf Ag | Verfahren zur Herstellung gamma,delta-ungesättigten Ketonen durch Caroll-Reaktion in cyclischen Carbonaten oder gamma-Lactonen als Lösungsmittel |
| US6051741A (en) * | 1997-10-17 | 2000-04-18 | Basf Aktiengesellschaft | Preparation of γ,δ-unsaturated ketones by the Carroll reaction, novel catalysts therefor and the preparation thereof |
-
1998
- 1998-09-07 DE DE19840746A patent/DE19840746A1/de not_active Withdrawn
-
1999
- 1999-09-02 CA CA002343521A patent/CA2343521A1/en not_active Abandoned
- 1999-09-02 EP EP99946093A patent/EP1112245A1/de not_active Withdrawn
- 1999-09-02 WO PCT/EP1999/006447 patent/WO2000014046A1/de not_active Application Discontinuation
- 1999-09-02 ID IDW20010546A patent/ID27392A/id unknown
- 1999-09-02 CN CN99812906A patent/CN1348434A/zh active Pending
- 1999-09-02 IL IL14168999A patent/IL141689A0/xx unknown
- 1999-09-02 JP JP2000568806A patent/JP2002524435A/ja not_active Withdrawn
- 1999-09-02 KR KR1020017002894A patent/KR20010074970A/ko not_active Application Discontinuation
- 1999-09-02 AU AU58583/99A patent/AU5858399A/en not_active Abandoned
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102050714A (zh) * | 2010-12-08 | 2011-05-11 | 成都自豪药业有限公司 | 一种合成替普瑞酮的方法 |
| CN102050714B (zh) * | 2010-12-08 | 2014-02-05 | 重庆恒韵医药有限公司 | 一种合成替普瑞酮的方法 |
| CN103058839A (zh) * | 2013-01-25 | 2013-04-24 | 四川源基制药有限公司 | 替普瑞酮合成及纯化工艺 |
| CN103058839B (zh) * | 2013-01-25 | 2014-12-17 | 四川源基制药有限公司 | 替普瑞酮合成及纯化工艺 |
| CN104513117A (zh) * | 2013-10-08 | 2015-04-15 | 中国科学院大连化学物理研究所 | 一种手性β-乙炔基酮化合物的催化不对称合成方法 |
| CN104513117B (zh) * | 2013-10-08 | 2016-08-10 | 中国科学院大连化学物理研究所 | 一种手性β-乙炔基酮化合物的催化不对称合成方法 |
| CN104326890A (zh) * | 2014-11-21 | 2015-02-04 | 山东新和成药业有限公司 | 一种Carroll反应连续化工艺方法 |
| CN104326890B (zh) * | 2014-11-21 | 2016-08-24 | 山东新和成药业有限公司 | 一种Carroll反应连续化工艺方法 |
| CN116212943A (zh) * | 2022-12-05 | 2023-06-06 | 江苏宏邦化工科技有限公司 | 一种新型碱性催化剂的制备方法及其在制备甲基庚烯酮中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| ID27392A (id) | 2001-04-05 |
| EP1112245A1 (de) | 2001-07-04 |
| WO2000014046A1 (de) | 2000-03-16 |
| AU5858399A (en) | 2000-03-27 |
| CA2343521A1 (en) | 2000-03-16 |
| JP2002524435A (ja) | 2002-08-06 |
| KR20010074970A (ko) | 2001-08-09 |
| IL141689A0 (en) | 2002-03-10 |
| DE19840746A1 (de) | 2000-03-09 |
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