FI72722C - Foerfarande foer framstaellning av 3-hydroxi-4-pyroner. - Google Patents
Foerfarande foer framstaellning av 3-hydroxi-4-pyroner. Download PDFInfo
- Publication number
- FI72722C FI72722C FI771934A FI771934A FI72722C FI 72722 C FI72722 C FI 72722C FI 771934 A FI771934 A FI 771934A FI 771934 A FI771934 A FI 771934A FI 72722 C FI72722 C FI 72722C
- Authority
- FI
- Finland
- Prior art keywords
- pyrone
- hydroxy
- formula
- dihydro
- methyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 27
- VEYIMQVTPXPUHA-UHFFFAOYSA-N 3-hydroxypyran-4-one Chemical class OC1=COC=CC1=O VEYIMQVTPXPUHA-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052794 bromium Chemical group 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 38
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 239000007800 oxidant agent Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 13
- 230000001590 oxidative effect Effects 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- 150000002431 hydrogen Chemical group 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 1-piperidylmethyl Chemical group 0.000 description 8
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229940043353 maltol Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 6
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- BOABLGZTHBBHPW-UHFFFAOYSA-N 2-hydroxy-2h-pyran-5-one Chemical class OC1OCC(=O)C=C1 BOABLGZTHBBHPW-UHFFFAOYSA-N 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- DSEPAHSEUBGYDG-UHFFFAOYSA-N 4-bromo-2-hydroxy-6-methyl-2h-pyran-5-one Chemical compound CC1OC(O)C=C(Br)C1=O DSEPAHSEUBGYDG-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- 239000002024 ethyl acetate extract Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UABXUIWIFUZYQK-UHFFFAOYSA-N 1-(furan-2-yl)ethanol Chemical compound CC(O)C1=CC=CO1 UABXUIWIFUZYQK-UHFFFAOYSA-N 0.000 description 3
- DHPZIGNTAGIVKP-UHFFFAOYSA-N 4-chloro-2-methoxy-6-methyl-2h-pyran-5-one Chemical compound COC1OC(C)C(=O)C(Cl)=C1 DHPZIGNTAGIVKP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- NVSWJFYXSKAOMG-UHFFFAOYSA-N (4-bromo-5-oxo-2h-pyran-2-yl) acetate Chemical compound CC(=O)OC1OCC(=O)C(Br)=C1 NVSWJFYXSKAOMG-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- CSEDVMRKXMDBAK-UHFFFAOYSA-N 2-methoxy-6-methyl-2h-pyran-5-one Chemical compound COC1OC(C)C(=O)C=C1 CSEDVMRKXMDBAK-UHFFFAOYSA-N 0.000 description 2
- SZEBFBITOQGJBK-UHFFFAOYSA-N 4-bromo-2-methoxy-6-methyl-2h-pyran-5-one Chemical compound COC1OC(C)C(=O)C(Br)=C1 SZEBFBITOQGJBK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- SMQYGPIQCFSJKL-UHFFFAOYSA-N (4-bromo-6-methyl-5-oxo-2h-pyran-2-yl) acetate Chemical compound CC1OC(OC(C)=O)C=C(Br)C1=O SMQYGPIQCFSJKL-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
- GMRFAZZMYGJAQO-UHFFFAOYSA-N (6-methyl-5-oxo-2h-pyran-2-yl) acetate Chemical compound CC1OC(OC(C)=O)C=CC1=O GMRFAZZMYGJAQO-UHFFFAOYSA-N 0.000 description 1
- OXXDGKNPRNPMLS-UHFFFAOYSA-N 2-Hydroxy-3-methyl-4H-pyran-4-one Natural products CC1=C(O)OC=CC1=O OXXDGKNPRNPMLS-UHFFFAOYSA-N 0.000 description 1
- MGVKFOXKPFXROH-UHFFFAOYSA-N 2-ethyl-3-hydroxy-6-methylpyran-4-one Chemical compound CCC=1OC(C)=CC(=O)C=1O MGVKFOXKPFXROH-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
- BOUVETHTKDBTIB-UHFFFAOYSA-N 2h-pyran-6-yl 3-chlorobenzoate Chemical class ClC1=CC=CC(C(=O)OC=2OCC=CC=2)=C1 BOUVETHTKDBTIB-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-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
- YQIUCEVQCDXCBS-UHFFFAOYSA-N 4-bromo-2-[(4-bromo-6-methyl-5-oxo-2h-pyran-2-yl)oxy]-6-methyl-2h-pyran-5-one Chemical compound C1=C(Br)C(=O)C(C)OC1OC1C=C(Br)C(=O)C(C)O1 YQIUCEVQCDXCBS-UHFFFAOYSA-N 0.000 description 1
- DQYZMWTXNWIUNS-UHFFFAOYSA-N 4-bromo-2-hydroxy-2h-pyran-5-one Chemical compound OC1OCC(=O)C(Br)=C1 DQYZMWTXNWIUNS-UHFFFAOYSA-N 0.000 description 1
- TXCADDUIVINZSC-UHFFFAOYSA-N 4-bromo-6-ethyl-2-hydroxy-2h-pyran-5-one Chemical compound CCC1OC(O)C=C(Br)C1=O TXCADDUIVINZSC-UHFFFAOYSA-N 0.000 description 1
- IGMQAWRMDKAASU-UHFFFAOYSA-N 4-chloro-2-hydroxy-2h-pyran-5-one Chemical compound OC1OCC(=O)C(Cl)=C1 IGMQAWRMDKAASU-UHFFFAOYSA-N 0.000 description 1
- UIYKATFGIGUNGC-UHFFFAOYSA-N 4-chloro-2-hydroxy-6-methyl-2h-pyran-5-one Chemical compound CC1OC(O)C=C(Cl)C1=O UIYKATFGIGUNGC-UHFFFAOYSA-N 0.000 description 1
- IBSOWVDZAXZPTI-UHFFFAOYSA-N 4-chloro-6-ethyl-2-hydroxy-2h-pyran-5-one Chemical compound CCC1OC(O)C=C(Cl)C1=O IBSOWVDZAXZPTI-UHFFFAOYSA-N 0.000 description 1
- ZWZWDOVLEINXRB-UHFFFAOYSA-N 6-hydroxy-6-methyl-2H-pyran-5-one Chemical compound CC1(O)OCC=CC1=O ZWZWDOVLEINXRB-UHFFFAOYSA-N 0.000 description 1
- 229910014265 BrCl Inorganic materials 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000723343 Cichorium Species 0.000 description 1
- 235000007542 Cichorium intybus Nutrition 0.000 description 1
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 1
- 241000218652 Larix Species 0.000 description 1
- 235000005590 Larix decidua Nutrition 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-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
- 239000006227 byproduct Substances 0.000 description 1
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 229940093503 ethyl maltol Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000007811 spectroscopic assay Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Cosmetics (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Transforming Electric Information Into Light Information (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Picture Signal Circuits (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Processing Of Color Television Signals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Control Of El Displays (AREA)
- Seasonings (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI831703A FI73424C (fi) | 1976-08-02 | 1983-05-16 | Foerfarande foer framstaellning av en som mellanprodukt vid 3-hydroxi-4-pyronframstaellningen anvaendbar 4-halogen- 6-(alkoxi eller alkanoyloxi)-2,6-dihydro-3-pyron. |
| FI831704A FI72721C (fi) | 1976-08-02 | 1983-05-16 | Vid framstaellning av gamma-pyroner saosom mellanprodukt anvaendbar 6,6'oxi-bis/4-halogen-2,6-dihydro-3-pyron/ och foerfarande foer dess framstaellning. |
| FI831700A FI72119C (fi) | 1976-08-02 | 1983-05-16 | Foerfarande foer framstaellning av 2-alkyl-3-hydroxi-4-pyroner. |
| FI831702A FI72720C (fi) | 1976-08-02 | 1983-05-16 | 4-halogen-dihydropyronfoerening foer anvaendning som mellanprodukt vid framstaellningen av 3-hydroxi-4-pyroner och foerfarande foer dess framstaellning. |
| FI831701A FI72723C (fi) | 1976-08-02 | 1983-05-16 | Foerfarande foer framstaellning av 3-hydroxi-4-pyroner. |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71090176A | 1976-08-02 | 1976-08-02 | |
| US71090176 | 1976-08-02 | ||
| US05/721,885 US4082717A (en) | 1976-08-02 | 1976-09-09 | Preparation of gamma-pyrones |
| US72188576 | 1976-09-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771934A7 FI771934A7 (enrdf_load_stackoverflow) | 1978-02-03 |
| FI72722B FI72722B (fi) | 1987-03-31 |
| FI72722C true FI72722C (fi) | 1987-07-10 |
Family
ID=27108548
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771934A FI72722C (fi) | 1976-08-02 | 1977-06-21 | Foerfarande foer framstaellning av 3-hydroxi-4-pyroner. |
| FI831702A FI72720C (fi) | 1976-08-02 | 1983-05-16 | 4-halogen-dihydropyronfoerening foer anvaendning som mellanprodukt vid framstaellningen av 3-hydroxi-4-pyroner och foerfarande foer dess framstaellning. |
| FI831704A FI72721C (fi) | 1976-08-02 | 1983-05-16 | Vid framstaellning av gamma-pyroner saosom mellanprodukt anvaendbar 6,6'oxi-bis/4-halogen-2,6-dihydro-3-pyron/ och foerfarande foer dess framstaellning. |
| FI831700A FI72119C (fi) | 1976-08-02 | 1983-05-16 | Foerfarande foer framstaellning av 2-alkyl-3-hydroxi-4-pyroner. |
| FI831701A FI72723C (fi) | 1976-08-02 | 1983-05-16 | Foerfarande foer framstaellning av 3-hydroxi-4-pyroner. |
| FI831703A FI73424C (fi) | 1976-08-02 | 1983-05-16 | Foerfarande foer framstaellning av en som mellanprodukt vid 3-hydroxi-4-pyronframstaellningen anvaendbar 4-halogen- 6-(alkoxi eller alkanoyloxi)-2,6-dihydro-3-pyron. |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI831702A FI72720C (fi) | 1976-08-02 | 1983-05-16 | 4-halogen-dihydropyronfoerening foer anvaendning som mellanprodukt vid framstaellningen av 3-hydroxi-4-pyroner och foerfarande foer dess framstaellning. |
| FI831704A FI72721C (fi) | 1976-08-02 | 1983-05-16 | Vid framstaellning av gamma-pyroner saosom mellanprodukt anvaendbar 6,6'oxi-bis/4-halogen-2,6-dihydro-3-pyron/ och foerfarande foer dess framstaellning. |
| FI831700A FI72119C (fi) | 1976-08-02 | 1983-05-16 | Foerfarande foer framstaellning av 2-alkyl-3-hydroxi-4-pyroner. |
| FI831701A FI72723C (fi) | 1976-08-02 | 1983-05-16 | Foerfarande foer framstaellning av 3-hydroxi-4-pyroner. |
| FI831703A FI73424C (fi) | 1976-08-02 | 1983-05-16 | Foerfarande foer framstaellning av en som mellanprodukt vid 3-hydroxi-4-pyronframstaellningen anvaendbar 4-halogen- 6-(alkoxi eller alkanoyloxi)-2,6-dihydro-3-pyron. |
Country Status (36)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1095921A (en) | 1976-08-02 | 1981-02-17 | Thomas M. Brennan | Preparation of gamma-pyrones |
| FR2402654A1 (fr) * | 1977-09-12 | 1979-04-06 | Shinetsu Chemical Co | Nouveaux derives de x tetrahydropyrannone(5) |
| JPS5444675A (en) * | 1977-09-12 | 1979-04-09 | Shin Etsu Chem Co Ltd | Production of 3-hydroxy-4-pyrone analog |
| JPS5741226U (enrdf_load_stackoverflow) * | 1980-08-20 | 1982-03-05 | ||
| JPS59135008U (ja) * | 1983-02-28 | 1984-09-10 | 松下電工株式会社 | 分電盤装置 |
| JPS6050245A (ja) * | 1983-08-29 | 1985-03-19 | Nissan Motor Co Ltd | 内燃機関の燃料噴射装置 |
| JPH0226945Y2 (enrdf_load_stackoverflow) * | 1985-09-11 | 1990-07-20 | ||
| JP2586607B2 (ja) * | 1987-10-30 | 1997-03-05 | 日産化学工業株式会社 | 光学活性アルコールの製造法 |
| MX2009010407A (es) * | 2007-03-28 | 2009-12-01 | Apotex Technologies Inc | Derivados fluorados de deferiprona. |
| WO2009129592A1 (en) | 2008-04-25 | 2009-10-29 | Apotex Technologies Inc. | Liquid formulation for deferiprone with palatable taste |
| US9073865B2 (en) | 2009-07-03 | 2015-07-07 | Apotex Technologies Inc. | Fluorinated derivates of 3-hydroxypyridin-4-ones |
| WO2017168309A1 (en) * | 2016-03-29 | 2017-10-05 | Dr. Reddy’S Laboratories Limited | Process for preparation of eribulin and intermediates thereof |
| CN108609456B (zh) * | 2016-12-13 | 2021-03-12 | 奥的斯电梯公司 | 可打开扩展面板及具有其的电梯吊顶，轿厢和系统 |
| CN111606879A (zh) * | 2020-05-25 | 2020-09-01 | 安徽金禾实业股份有限公司 | 一锅法制备2-羟甲基-3-烷氧基-4h-吡喃-4-酮的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3491122A (en) * | 1966-09-14 | 1970-01-20 | Monsanto Co | Synthesis of 4-pyrones |
| US3547912A (en) * | 1968-07-29 | 1970-12-15 | American Home Prod | Derivatives of 2h-pyran-3(6h)-ones and preparation thereof |
| JPS5145565B1 (enrdf_load_stackoverflow) * | 1968-10-12 | 1976-12-04 | ||
| US3621063A (en) * | 1968-12-24 | 1971-11-16 | Monsanto Co | Unsaturated acyclic ketones |
| US3832357A (en) * | 1971-05-26 | 1974-08-27 | Daicel Ltd | Process for preparation of 3-hydroxy-2-alkyl-4-pyrone |
| JPS5212166A (en) * | 1975-07-17 | 1977-01-29 | Tatsuya Shono | Process for preparation of 4-pyron derivatives |
| IE42789B1 (en) * | 1975-08-28 | 1980-10-22 | Pfizer | Preparation of gamma-pyrones |
| CA1095921A (en) | 1976-08-02 | 1981-02-17 | Thomas M. Brennan | Preparation of gamma-pyrones |
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1977
- 1977-06-06 CA CA279,922A patent/CA1095921A/en not_active Expired
- 1977-06-08 NZ NZ184342A patent/NZ184342A/xx unknown
- 1977-06-09 GR GR53666A patent/GR68938B/el unknown
- 1977-06-13 YU YU1469/77A patent/YU40166B/xx unknown
- 1977-06-15 MX MX775807U patent/MX4597E/es unknown
- 1977-06-16 JP JP7157277A patent/JPS5318578A/ja active Granted
- 1977-06-16 SE SE7707035A patent/SE433079B/xx not_active IP Right Cessation
- 1977-06-17 PH PH19887A patent/PH13557A/en unknown
- 1977-06-20 BR BR7703970A patent/BR7703970A/pt unknown
- 1977-06-21 BE BE1008209A patent/BE855965A/xx not_active IP Right Cessation
- 1977-06-21 FI FI771934A patent/FI72722C/fi not_active IP Right Cessation
- 1977-06-21 NL NLAANVRAGE7706811,A patent/NL170955C/xx not_active IP Right Cessation
- 1977-06-22 ES ES459994A patent/ES459994A1/es not_active Expired
- 1977-06-22 AT AT0440477A patent/AT362790B/de not_active IP Right Cessation
- 1977-06-22 PT PT66694A patent/PT66694B/pt unknown
- 1977-06-22 LU LU77600A patent/LU77600A1/xx unknown
- 1977-06-22 EG EG371/77A patent/EG13080A/xx active
- 1977-06-22 DK DK276177A patent/DK153483C/da active
- 1977-06-22 DE DE2728499A patent/DE2728499C2/de not_active Expired
- 1977-06-22 DE DE2760220A patent/DE2760220C2/de not_active Expired
- 1977-06-22 NO NO772193A patent/NO150561C/no unknown
- 1977-06-22 DE DE2760221A patent/DE2760221C2/de not_active Expired
- 1977-06-22 TR TR19652A patent/TR19652A/xx unknown
- 1977-06-22 CH CH765877A patent/CH625798A5/fr not_active IP Right Cessation
- 1977-06-23 AR AR268164A patent/AR216080A1/es active
- 1977-06-23 FR FR7719250A patent/FR2372821A1/fr active Granted
- 1977-06-23 IT IT49950/77A patent/IT1106258B/it active
- 1977-06-23 DD DD7700199657A patent/DD132494A5/xx not_active IP Right Cessation
- 1977-07-14 BG BG7942607A patent/BG28989A4/xx unknown
- 1977-07-14 CS CS774705A patent/CS203921B2/cs unknown
- 1977-07-14 BG BG7742606A patent/BG28988A4/xx unknown
- 1977-07-14 BG BG042608A patent/BG29136A3/xx unknown
- 1977-07-14 BG BG036892A patent/BG28849A3/xx unknown
- 1977-07-20 RO RO7799830A patent/RO78953A/ro unknown
- 1977-07-20 RO RO7799825A patent/RO78951A2/ro unknown
- 1977-07-20 RO RO7799826A patent/RO78952A/ro unknown
- 1977-07-20 RO RO7791106A patent/RO74367A/ro unknown
- 1977-07-21 GB GB4240/78A patent/GB1538372A/en not_active Expired
- 1977-07-21 HU HU82156A patent/HU186026B/hu unknown
- 1977-07-21 HU HU77PI584A patent/HU180040B/hu unknown
- 1977-07-21 GB GB4241/78A patent/GB1538373A/en not_active Expired
- 1977-07-21 HU HU82155A patent/HU185686B/hu unknown
- 1977-07-21 SU SU772508256A patent/SU955859A3/ru active
- 1977-07-21 PL PL21500877A patent/PL215008A1/xx unknown
- 1977-07-21 GB GB4243/78A patent/GB1538375A/en not_active Expired
- 1977-07-21 GB GB30759/77A patent/GB1538371A/en not_active Expired
- 1977-07-21 PL PL1977199798A patent/PL115586B1/pl unknown
- 1977-07-21 PL PL1977215006A patent/PL115497B1/pl unknown
- 1977-07-21 HU HU82157A patent/HU185687B/hu unknown
- 1977-07-21 PL PL1977215007A patent/PL115496B1/pl unknown
- 1977-07-21 GB GB4242/78A patent/GB1538374A/en not_active Expired
- 1977-07-29 IE IE585/79A patent/IE45643B1/en not_active IP Right Cessation
- 1977-07-29 IE IE587/79A patent/IE45645B1/en not_active IP Right Cessation
- 1977-07-29 IE IE586/79A patent/IE45644B1/en not_active IP Right Cessation
- 1977-07-29 IE IE584/79A patent/IE45642B1/en not_active IP Right Cessation
- 1977-07-29 IE IE1587/77A patent/IE45641B1/en not_active IP Right Cessation
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1978
- 1978-02-03 PH PH20746A patent/PH13926A/en unknown
- 1978-02-03 PH PH20745A patent/PH15185A/en unknown
- 1978-05-25 JP JP6281978A patent/JPS5436268A/ja active Pending
- 1978-05-25 JP JP53062820A patent/JPS5814433B2/ja not_active Expired
- 1978-05-25 JP JP6281778A patent/JPS5436266A/ja active Pending
- 1978-05-25 JP JP6282178A patent/JPS5436270A/ja active Granted
- 1978-05-25 JP JP6281878A patent/JPS5436267A/ja active Granted
- 1978-05-25 JP JP6282278A patent/JPS5436271A/ja active Granted
- 1978-06-07 CS CS783706A patent/CS203923B2/cs unknown
- 1978-06-07 CS CS783705A patent/CS203922B2/cs unknown
- 1978-06-13 ES ES470745A patent/ES470745A1/es not_active Expired
- 1978-06-13 ES ES470743A patent/ES470743A1/es not_active Expired
- 1978-06-13 ES ES470744A patent/ES470744A1/es not_active Expired
- 1978-06-13 ES ES470746A patent/ES470746A1/es not_active Expired
- 1978-07-05 SU SU782631651A patent/SU1015826A3/ru active
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1979
- 1979-02-01 PH PH22150A patent/PH13874A/en unknown
- 1979-02-01 PH PH22149A patent/PH14625A/en unknown
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1980
- 1980-03-06 AT AT0124380A patent/AT364356B/de not_active IP Right Cessation
- 1980-03-06 AT AT0124480A patent/AT363470B/de not_active IP Right Cessation
- 1980-10-24 CA CA363,273A patent/CA1110254A/en not_active Expired
- 1980-10-24 CA CA000363274A patent/CA1117541A/en not_active Expired
- 1980-10-30 CH CH808580A patent/CH625235A5/fr not_active IP Right Cessation
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1981
- 1981-02-20 CH CH116181A patent/CH626358A5/fr not_active IP Right Cessation
- 1981-02-20 CH CH116081A patent/CH626357A5/fr not_active IP Right Cessation
- 1981-07-02 HK HK306/81A patent/HK30681A/xx unknown
- 1981-07-02 HK HK305/81A patent/HK30581A/xx unknown
- 1981-07-02 HK HK304/81A patent/HK30481A/xx unknown
- 1981-07-02 HK HK303/81A patent/HK30381A/en unknown
- 1981-07-02 HK HK307/81A patent/HK30781A/xx unknown
- 1981-12-09 NL NLAANVRAGE8105538,A patent/NL182477C/xx not_active IP Right Cessation
- 1981-12-09 NL NLAANVRAGE8105540,A patent/NL182805C/xx not_active IP Right Cessation
- 1981-12-09 NL NLAANVRAGE8105537,A patent/NL182476C/xx not_active IP Right Cessation
- 1981-12-09 NL NLAANVRAGE8105539,A patent/NL182478C/xx not_active IP Right Cessation
- 1981-12-30 MY MY267/81A patent/MY8100267A/xx unknown
- 1981-12-30 MY MY262/81A patent/MY8100262A/xx unknown
- 1981-12-30 MY MY287/81A patent/MY8100287A/xx unknown
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1982
- 1982-01-29 SE SE8200521A patent/SE452616B/sv not_active IP Right Cessation
- 1982-01-29 SE SE8200522A patent/SE444565B/sv not_active IP Right Cessation
- 1982-01-29 SE SE8200518A patent/SE445041B/sv not_active IP Right Cessation
- 1982-01-29 SE SE8200519A patent/SE445042B/sv not_active IP Right Cessation
- 1982-01-29 SE SE8200520A patent/SE444564B/sv not_active IP Right Cessation
- 1982-06-03 NO NO821849A patent/NO150559C/no unknown
- 1982-06-03 NO NO821848A patent/NO150043C/no unknown
- 1982-06-03 NO NO821850A patent/NO821850L/no unknown
- 1982-06-03 NO NO821851A patent/NO150560C/no unknown
- 1982-06-03 NO NO821847A patent/NO150042C/no unknown
- 1982-12-07 YU YU02703/82A patent/YU270382A/xx unknown
- 1982-12-13 YU YU2747/82A patent/YU42613B/xx unknown
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1983
- 1983-05-16 FI FI831702A patent/FI72720C/fi not_active IP Right Cessation
- 1983-05-16 FI FI831704A patent/FI72721C/fi not_active IP Right Cessation
- 1983-05-16 FI FI831700A patent/FI72119C/fi not_active IP Right Cessation
- 1983-05-16 FI FI831701A patent/FI72723C/fi not_active IP Right Cessation
- 1983-05-16 FI FI831703A patent/FI73424C/fi not_active IP Right Cessation
- 1983-08-08 YU YU1663/83A patent/YU43190B/xx unknown
- 1983-11-18 NO NO834236A patent/NO151365C/no unknown
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1986
- 1986-07-09 DK DK325986A patent/DK153484C/da active
- 1986-07-09 DK DK326186A patent/DK154079C/da active
- 1986-07-09 DK DK326086A patent/DK153401C/da not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| PC | Transfer of assignment of patent |
Owner name: CULTOR OY |
|
| MA | Patent expired |
Owner name: CULTOR OY |