DE2608932C2 - Verfahren zur Herstellung von 3-Oxy-4H-pyran-4-on-Derivaten - Google Patents
Verfahren zur Herstellung von 3-Oxy-4H-pyran-4-on-DerivatenInfo
- Publication number
- DE2608932C2 DE2608932C2 DE2608932A DE2608932A DE2608932C2 DE 2608932 C2 DE2608932 C2 DE 2608932C2 DE 2608932 A DE2608932 A DE 2608932A DE 2608932 A DE2608932 A DE 2608932A DE 2608932 C2 DE2608932 C2 DE 2608932C2
- Authority
- DE
- Germany
- Prior art keywords
- pyran
- oxo
- dihydro
- ethoxy
- mixture
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- YYRYKNXDWXDXSN-UHFFFAOYSA-N 2h-pyran-5-one Chemical class O=C1COCC=C1 YYRYKNXDWXDXSN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- -1 2-ethyl Chemical group 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 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 description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- VPOBZOGAFVUGIX-UHFFFAOYSA-N 2-ethoxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CCOC1OC(C)C(=O)C2OC12 VPOBZOGAFVUGIX-UHFFFAOYSA-N 0.000 description 2
- OYRWCMASLRNSFD-UHFFFAOYSA-N 6-butyl-2-ethoxy-2h-pyran-5-one Chemical compound CCCCC1OC(OCC)C=CC1=O OYRWCMASLRNSFD-UHFFFAOYSA-N 0.000 description 2
- VYWBYISNYZSJLL-UHFFFAOYSA-N 6-ethyl-2-methoxy-2h-pyran-5-one Chemical compound CCC1OC(OC)C=CC1=O VYWBYISNYZSJLL-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- HBBBDGWCSBWWKP-UHFFFAOYSA-J tetrachloroantimony Chemical compound Cl[Sb](Cl)(Cl)Cl HBBBDGWCSBWWKP-UHFFFAOYSA-J 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- NQVZPBPVMSMYIJ-UHFFFAOYSA-N (4-methyl-5-oxo-3,7-dioxabicyclo[4.1.0]heptan-2-yl) 2-methylpropanoate Chemical compound CC(C)C(=O)OC1OC(C)C(=O)C2OC12 NQVZPBPVMSMYIJ-UHFFFAOYSA-N 0.000 description 1
- JJVMFCRCFSJODB-UHFFFAOYSA-N (5-oxo-2h-pyran-2-yl) acetate Chemical compound CC(=O)OC1OCC(=O)C=C1 JJVMFCRCFSJODB-UHFFFAOYSA-N 0.000 description 1
- GPFXVUVIEANTCR-UHFFFAOYSA-N (6-decyl-5-oxo-2h-pyran-2-yl) acetate Chemical compound CCCCCCCCCCC1OC(OC(C)=O)C=CC1=O GPFXVUVIEANTCR-UHFFFAOYSA-N 0.000 description 1
- HQNNAWMTSJWJFQ-UHFFFAOYSA-N (6-ethyl-5-oxo-2h-pyran-2-yl) acetate Chemical compound CCC1OC(OC(C)=O)C=CC1=O HQNNAWMTSJWJFQ-UHFFFAOYSA-N 0.000 description 1
- IUGLPYDEPCQOLP-UHFFFAOYSA-N (6-methyl-5-oxo-2h-pyran-2-yl) 2-methylpropanoate Chemical compound CC(C)C(=O)OC1OC(C)C(=O)C=C1 IUGLPYDEPCQOLP-UHFFFAOYSA-N 0.000 description 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical class CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- ZXNQSMFGPQEBKM-UHFFFAOYSA-N 2-butoxy-2h-pyran-5-one Chemical compound CCCCOC1OCC(=O)C=C1 ZXNQSMFGPQEBKM-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- YFWBNHSYXGFXLE-UHFFFAOYSA-N 2-ethoxy-2h-pyran-5-one Chemical compound CCOC1OCC(=O)C=C1 YFWBNHSYXGFXLE-UHFFFAOYSA-N 0.000 description 1
- BLBNCIKXDSXUIC-UHFFFAOYSA-N 2-ethoxy-4-ethyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CCOC1OC(CC)C(=O)C2OC12 BLBNCIKXDSXUIC-UHFFFAOYSA-N 0.000 description 1
- JCSZMSVNGHLLNB-UHFFFAOYSA-N 2-ethoxy-4-hexyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCCCC)OC(OCC)C2OC21 JCSZMSVNGHLLNB-UHFFFAOYSA-N 0.000 description 1
- BUCSXABEHCBNTH-UHFFFAOYSA-N 2-ethoxy-6-ethyl-2h-pyran-5-one Chemical compound CCOC1OC(CC)C(=O)C=C1 BUCSXABEHCBNTH-UHFFFAOYSA-N 0.000 description 1
- GFUMRMDKDPCWSE-UHFFFAOYSA-N 2-ethoxy-6-hexyl-2h-pyran-5-one Chemical compound CCCCCCC1OC(OCC)C=CC1=O GFUMRMDKDPCWSE-UHFFFAOYSA-N 0.000 description 1
- RZZDSHGXUWNGAV-UHFFFAOYSA-N 2-ethoxy-6-methyl-2h-pyran-5-one Chemical compound CCOC1OC(C)C(=O)C=C1 RZZDSHGXUWNGAV-UHFFFAOYSA-N 0.000 description 1
- OTFUSKNZLQKSFF-UHFFFAOYSA-N 2-ethoxy-6-octyl-2h-pyran-5-one Chemical compound CCCCCCCCC1OC(OCC)C=CC1=O OTFUSKNZLQKSFF-UHFFFAOYSA-N 0.000 description 1
- BDTOBOMFWCKGRG-UHFFFAOYSA-N 2-ethylpyran-3,4-dione Chemical compound CCC1OC=CC(=O)C1=O BDTOBOMFWCKGRG-UHFFFAOYSA-N 0.000 description 1
- BOABLGZTHBBHPW-UHFFFAOYSA-N 2-hydroxy-2h-pyran-5-one Chemical compound OC1OCC(=O)C=C1 BOABLGZTHBBHPW-UHFFFAOYSA-N 0.000 description 1
- PLYSJDAYJMFETG-UHFFFAOYSA-N 2-hydroxy-6-methyl-2h-pyran-5-one Chemical compound CC1OC(O)C=CC1=O PLYSJDAYJMFETG-UHFFFAOYSA-N 0.000 description 1
- DRGCDPHCOXNIIY-UHFFFAOYSA-N 2-methoxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound COC1OC(C)C(=O)C2OC12 DRGCDPHCOXNIIY-UHFFFAOYSA-N 0.000 description 1
- SOPBORCOCVQHJW-UHFFFAOYSA-N 2-methoxy-6-octyl-2h-pyran-5-one Chemical compound CCCCCCCCC1OC(OC)C=CC1=O SOPBORCOCVQHJW-UHFFFAOYSA-N 0.000 description 1
- QOBVYDFJCWOWOW-UHFFFAOYSA-N 2-propan-2-yloxy-2h-pyran-5-one Chemical compound CC(C)OC1OCC(=O)C=C1 QOBVYDFJCWOWOW-UHFFFAOYSA-N 0.000 description 1
- KFIDJGBHJNJNFC-UHFFFAOYSA-N 3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical class O=C1COCC2OC12 KFIDJGBHJNJNFC-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XIPGMIWMZXBKGS-UHFFFAOYSA-N 4-butyl-2-ethoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCC)OC(OCC)C2OC21 XIPGMIWMZXBKGS-UHFFFAOYSA-N 0.000 description 1
- MRUWJENAYHTDQG-UHFFFAOYSA-N 4H-pyran Chemical compound C1C=COC=C1 MRUWJENAYHTDQG-UHFFFAOYSA-N 0.000 description 1
- ATBJWHYEJAHPHD-UHFFFAOYSA-N 6-butyl-2-methoxy-2h-pyran-5-one Chemical compound CCCCC1OC(OC)C=CC1=O ATBJWHYEJAHPHD-UHFFFAOYSA-N 0.000 description 1
- BLVHQERCCDOEJG-UHFFFAOYSA-N 6-decyl-2-ethoxy-2h-pyran-5-one Chemical compound CCCCCCCCCCC1OC(OCC)C=CC1=O BLVHQERCCDOEJG-UHFFFAOYSA-N 0.000 description 1
- REGQVCXIQLCNMD-UHFFFAOYSA-N 6-decyl-2-methoxy-2h-pyran-5-one Chemical compound CCCCCCCCCCC1OC(OC)C=CC1=O REGQVCXIQLCNMD-UHFFFAOYSA-N 0.000 description 1
- YUTAFCIWIJWQIX-UHFFFAOYSA-N 6-ethyl-2-hydroxy-2h-pyran-5-one Chemical compound CCC1OC(O)C=CC1=O YUTAFCIWIJWQIX-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 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
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Epoxy Compounds (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50087940A JPS5212166A (en) | 1975-07-17 | 1975-07-17 | Process for preparation of 4-pyron derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2608932A1 DE2608932A1 (de) | 1977-01-20 |
| DE2608932C2 true DE2608932C2 (de) | 1982-07-08 |
Family
ID=13928886
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2608932A Expired DE2608932C2 (de) | 1975-07-17 | 1976-03-04 | Verfahren zur Herstellung von 3-Oxy-4H-pyran-4-on-Derivaten |
| DE2609888A Expired DE2609888C3 (de) | 1975-07-17 | 1976-03-10 | 4,5-Epoxy-3-oxo-tetrahydopyran-Derivate, Verfahren zu deren Herstellung und bacterizides und fungizides Mittel mit einem Gehalt dieser Verbindungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2609888A Expired DE2609888C3 (de) | 1975-07-17 | 1976-03-10 | 4,5-Epoxy-3-oxo-tetrahydopyran-Derivate, Verfahren zu deren Herstellung und bacterizides und fungizides Mittel mit einem Gehalt dieser Verbindungen |
Country Status (8)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4342697A (en) * | 1975-08-28 | 1982-08-03 | Pfizer Inc. | Preparation of gamma-pyrones |
| IE42789B1 (en) * | 1975-08-28 | 1980-10-22 | Pfizer | Preparation of gamma-pyrones |
| JPS532468A (en) * | 1976-06-15 | 1978-01-11 | Otsuka Chem Co Ltd | 2,2-bis(3,4-epoxy-5-oxotetrahydropyrane)-ethers and method of preparing the same |
| CA1095921A (en) * | 1976-08-02 | 1981-02-17 | Thomas M. Brennan | Preparation of gamma-pyrones |
| JPS5353613U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1976-10-11 | 1978-05-09 | ||
| US4390709A (en) * | 1976-11-11 | 1983-06-28 | Pfizer Inc. | Preparation of gamma-pyrones |
| US4191693A (en) * | 1976-11-12 | 1980-03-04 | Pfizer, Inc. | Preparation of gamma-pyrones from 3-substituted furans |
| JPS5481273A (en) * | 1977-12-12 | 1979-06-28 | Shin Etsu Chem Co Ltd | Preparation of pyranone halide |
| US4451661A (en) * | 1982-04-26 | 1984-05-29 | Pfizer Inc. | Preparation of gamma-pyrone intermediates |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159652A (en) * | 1962-06-13 | 1964-12-01 | Pfizer & Co C | Preparation of gamma-pyrones |
| US3476778A (en) * | 1966-05-16 | 1969-11-04 | Monsanto Co | Gamma-pyrone synthesis |
| US3491122A (en) * | 1966-09-14 | 1970-01-20 | Monsanto Co | Synthesis of 4-pyrones |
| JPS5145565B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-10-12 | 1976-12-04 |
-
1975
- 1975-07-17 JP JP50087940A patent/JPS5212166A/ja active Granted
-
1976
- 1976-02-25 GB GB7539/76A patent/GB1498365A/en not_active Expired
- 1976-02-26 US US05/661,823 patent/US4059595A/en not_active Expired - Lifetime
- 1976-02-26 GB GB7540/76A patent/GB1496992A/en not_active Expired
- 1976-03-04 DE DE2608932A patent/DE2608932C2/de not_active Expired
- 1976-03-05 CH CH281676A patent/CH617200A5/de not_active IP Right Cessation
- 1976-03-05 CH CH281776A patent/CH619700A5/de not_active IP Right Cessation
- 1976-03-05 IT IT20921/76A patent/IT1063916B/it active
- 1976-03-05 FR FR7606288A patent/FR2318161A1/fr active Granted
- 1976-03-09 IT IT21011/76A patent/IT1063914B/it active
- 1976-03-10 DE DE2609888A patent/DE2609888C3/de not_active Expired
- 1976-03-10 FR FR7606779A patent/FR2317921A1/fr active Granted
- 1976-07-16 BE BE2055186A patent/BE844193A/xx not_active IP Right Cessation
- 1976-07-16 BE BE2055187A patent/BE844194A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2317921A1 (fr) | 1977-02-11 |
| GB1496992A (en) | 1978-01-05 |
| DE2609888A1 (de) | 1977-01-20 |
| DE2609888B2 (de) | 1978-09-07 |
| CH617200A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-14 |
| JPS5412465B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-23 |
| DE2608932A1 (de) | 1977-01-20 |
| BE844193A (fr) | 1976-11-16 |
| IT1063916B (it) | 1985-02-18 |
| FR2318161B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-08-25 |
| DE2609888C3 (de) | 1979-05-10 |
| CH619700A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-10-15 |
| BE844194A (fr) | 1976-11-16 |
| US4059595A (en) | 1977-11-22 |
| IT1063914B (it) | 1985-02-18 |
| FR2318161A1 (fr) | 1977-02-11 |
| FR2317921B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-09-22 |
| JPS5212166A (en) | 1977-01-29 |
| GB1498365A (en) | 1978-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |