NO773868L - Fremgangsmaate for fremstilling av gamma-pyroner - Google Patents
Fremgangsmaate for fremstilling av gamma-pyronerInfo
- Publication number
- NO773868L NO773868L NO773868A NO773868A NO773868L NO 773868 L NO773868 L NO 773868L NO 773868 A NO773868 A NO 773868A NO 773868 A NO773868 A NO 773868A NO 773868 L NO773868 L NO 773868L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- formula
- acid
- stated
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 58
- 238000002360 preparation method Methods 0.000 title description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 239000000460 chlorine Substances 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 28
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 claims description 25
- -1 chloro, bromo, iodo Chemical group 0.000 claims description 23
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical class OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000006460 hydrolysis reaction Methods 0.000 claims description 18
- 239000007800 oxidant agent Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 230000007062 hydrolysis Effects 0.000 claims description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 10
- 150000004965 peroxy acids Chemical class 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000002978 peroxides Chemical class 0.000 claims description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000006184 cosolvent Substances 0.000 claims description 7
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- DKSMCEUSSQTGBK-UHFFFAOYSA-N bromous acid Chemical compound OBr=O DKSMCEUSSQTGBK-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 239000011630 iodine Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000002240 furans Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- BOABLGZTHBBHPW-UHFFFAOYSA-N 2-hydroxy-2h-pyran-5-one Chemical class OC1OCC(=O)C=C1 BOABLGZTHBBHPW-UHFFFAOYSA-N 0.000 claims description 2
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 29
- 229940043353 maltol Drugs 0.000 description 23
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000001298 alcohols Chemical class 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- 238000000605 extraction Methods 0.000 description 10
- HPIGCVXMBGOWTF-UHFFFAOYSA-N isomaltol Chemical compound CC(=O)C=1OC=CC=1O HPIGCVXMBGOWTF-UHFFFAOYSA-N 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NDPORQIUDGZDFC-UHFFFAOYSA-N 1-(2,4,5-trimethoxy-2h-furan-5-yl)ethanol Chemical compound COC1OC(OC)(C(C)O)C(OC)=C1 NDPORQIUDGZDFC-UHFFFAOYSA-N 0.000 description 4
- DZHVHQHHGKDZGZ-UHFFFAOYSA-N 1-(3-methoxyfuran-2-yl)ethanol Chemical compound COC=1C=COC=1C(C)O DZHVHQHHGKDZGZ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 238000010517 secondary reaction Methods 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
- HFZDUEVKCBZGMZ-UHFFFAOYSA-N 1-(3-bromofuran-2-yl)ethanol Chemical compound CC(O)C=1OC=CC=1Br HFZDUEVKCBZGMZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ATULXGXSSCNYHE-UHFFFAOYSA-N 1-(3-bromo-2,5-dimethoxy-3h-furan-2-yl)ethanol Chemical compound COC1=CC(Br)C(OC)(C(C)O)O1 ATULXGXSSCNYHE-UHFFFAOYSA-N 0.000 description 2
- KAUYAIWEKCWPQL-UHFFFAOYSA-N 1-(3-chlorofuran-2-yl)ethanol Chemical compound CC(O)C=1OC=CC=1Cl KAUYAIWEKCWPQL-UHFFFAOYSA-N 0.000 description 2
- JPBHBYXIRVPJBY-UHFFFAOYSA-N 1-(3-chlorofuran-2-yl)ethanone Chemical compound CC(=O)C=1OC=CC=1Cl JPBHBYXIRVPJBY-UHFFFAOYSA-N 0.000 description 2
- PEYCUVYKPFIYHB-UHFFFAOYSA-N 2,4-dimethoxy-6-methyl-2h-pyran-5-one Chemical compound COC1OC(C)C(=O)C(OC)=C1 PEYCUVYKPFIYHB-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- VEYIMQVTPXPUHA-UHFFFAOYSA-N 3-hydroxypyran-4-one Chemical compound OC1=COC=CC1=O VEYIMQVTPXPUHA-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940093503 ethyl maltol Drugs 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical class O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JSIYXXPMVPHYJR-UHFFFAOYSA-N 1-(2,4,5-trimethoxy-2h-furan-5-yl)ethanone Chemical compound COC1OC(OC)(C(C)=O)C(OC)=C1 JSIYXXPMVPHYJR-UHFFFAOYSA-N 0.000 description 1
- VVNAWNFHVRSZPQ-UHFFFAOYSA-N 1-(3-bromo-2,5-dimethyl-3H-furan-2-yl)ethanol Chemical compound OC(C)C1(OC(=CC1Br)C)C VVNAWNFHVRSZPQ-UHFFFAOYSA-N 0.000 description 1
- QPZZLTOSEPARRM-UHFFFAOYSA-N 1-(3-bromofuran-2-yl)ethanone Chemical compound CC(=O)C=1OC=CC=1Br QPZZLTOSEPARRM-UHFFFAOYSA-N 0.000 description 1
- UABXUIWIFUZYQK-UHFFFAOYSA-N 1-(furan-2-yl)ethanol Chemical class CC(O)C1=CC=CO1 UABXUIWIFUZYQK-UHFFFAOYSA-N 0.000 description 1
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-Dihydrofuran Natural products C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 description 1
- DWKNOLCXIFYNFV-HSZRJFAPSA-N 2-[[(2r)-1-[1-[(4-chloro-3-methylphenyl)methyl]piperidin-4-yl]-5-oxopyrrolidine-2-carbonyl]amino]-n,n,6-trimethylpyridine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC(C)=NC(NC(=O)[C@@H]2N(C(=O)CC2)C2CCN(CC=3C=C(C)C(Cl)=CC=3)CC2)=C1 DWKNOLCXIFYNFV-HSZRJFAPSA-N 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000723343 Cichorium Species 0.000 description 1
- 235000007542 Cichorium intybus Nutrition 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 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 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000218652 Larix Species 0.000 description 1
- 235000005590 Larix decidua 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
- 241000276498 Pollachius virens Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 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
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude 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
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography 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
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical class 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 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C07D309/34—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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Seasonings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/741,348 US4126624A (en) | 1976-11-12 | 1976-11-12 | Preparation of gamma-pyrones from 3-substituted furans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO773868L true NO773868L (no) | 1978-05-16 |
Family
ID=24980357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO773868A NO773868L (no) | 1976-11-12 | 1977-11-11 | Fremgangsmaate for fremstilling av gamma-pyroner |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4126624A (de) |
| JP (2) | JPS5363381A (de) |
| AR (1) | AR217267A1 (de) |
| AU (1) | AU499476B1 (de) |
| BE (1) | BE860699A (de) |
| BR (1) | BR7707529A (de) |
| CA (1) | CA1109478A (de) |
| DD (1) | DD134349A5 (de) |
| DE (1) | DE2750553C2 (de) |
| DK (1) | DK502077A (de) |
| ES (1) | ES464045A1 (de) |
| FI (1) | FI773367A (de) |
| FR (2) | FR2385710A1 (de) |
| GB (1) | GB1543897A (de) |
| IE (1) | IE46411B1 (de) |
| IT (1) | IT1109435B (de) |
| LU (1) | LU78503A1 (de) |
| MX (1) | MX4750E (de) |
| NL (1) | NL167163C (de) |
| NO (1) | NO773868L (de) |
| PL (1) | PL202091A1 (de) |
| PT (1) | PT67234B (de) |
| SE (1) | SE7711964L (de) |
| TR (1) | TR19727A (de) |
| ZA (1) | ZA776744B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5481273A (en) * | 1977-12-12 | 1979-06-28 | Shin Etsu Chem Co Ltd | Preparation of pyranone halide |
| JPS59192558U (ja) * | 1983-06-07 | 1984-12-20 | 株式会社多川工業 | 粉砕機等のア−ム旋回装置 |
| 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 |
| RU2109739C1 (ru) * | 1994-01-31 | 1998-04-27 | Калтор Лтд. | Способы получения гамма-пиронов |
| CN107089962B (zh) * | 2017-04-18 | 2019-09-10 | 山东新和成药业有限公司 | 一种由分子氧氧化制备麦芽酚及同系物的方法 |
| CN111533719B (zh) * | 2020-04-29 | 2022-04-01 | 广东省肇庆华格生物科技有限公司 | 一种乙基麦芽酚的合成工艺 |
| CN112778257A (zh) * | 2021-01-21 | 2021-05-11 | 香港科技大学 | 一种将糠醇氧化为二氢吡喃酮类衍生物的绿色方法 |
Family Cites Families (3)
| 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 |
| US3832357A (en) * | 1971-05-26 | 1974-08-27 | Daicel Ltd | Process for preparation of 3-hydroxy-2-alkyl-4-pyrone |
-
1976
- 1976-11-12 US US05/741,348 patent/US4126624A/en not_active Expired - Lifetime
-
1977
- 1977-10-14 AU AU29689/77A patent/AU499476B1/en not_active Expired
- 1977-10-24 SE SE7711964A patent/SE7711964L/xx unknown
- 1977-11-03 PT PT67234A patent/PT67234B/pt unknown
- 1977-11-03 MX MX776518U patent/MX4750E/es unknown
- 1977-11-08 IT IT51737/77A patent/IT1109435B/it active
- 1977-11-08 TR TR19727A patent/TR19727A/xx unknown
- 1977-11-08 JP JP13405277A patent/JPS5363381A/ja active Granted
- 1977-11-09 GB GB46568/77A patent/GB1543897A/en not_active Expired
- 1977-11-09 FI FI773367A patent/FI773367A/fi not_active Application Discontinuation
- 1977-11-10 BR BR7707529A patent/BR7707529A/pt unknown
- 1977-11-10 CA CA290,679A patent/CA1109478A/en not_active Expired
- 1977-11-10 BE BE182521A patent/BE860699A/xx not_active IP Right Cessation
- 1977-11-10 FR FR7733949A patent/FR2385710A1/fr active Granted
- 1977-11-11 IE IE2296/77A patent/IE46411B1/en unknown
- 1977-11-11 DK DK502077A patent/DK502077A/da not_active Application Discontinuation
- 1977-11-11 DE DE2750553A patent/DE2750553C2/de not_active Expired
- 1977-11-11 ZA ZA00776744A patent/ZA776744B/xx unknown
- 1977-11-11 NL NL7712427.A patent/NL167163C/xx not_active IP Right Cessation
- 1977-11-11 AR AR269941A patent/AR217267A1/es active
- 1977-11-11 ES ES464045A patent/ES464045A1/es not_active Expired
- 1977-11-11 NO NO773868A patent/NO773868L/no unknown
- 1977-11-11 DD DD77202032A patent/DD134349A5/de unknown
- 1977-11-11 LU LU78503A patent/LU78503A1/xx unknown
- 1977-11-12 PL PL20209177A patent/PL202091A1/xx unknown
-
1978
- 1978-04-07 FR FR7810404A patent/FR2387973A1/fr active Granted
-
1979
- 1979-05-16 JP JP54060248A patent/JPS5814434B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR217267A1 (es) | 1980-03-14 |
| FR2387973B1 (de) | 1983-02-25 |
| JPS5363381A (en) | 1978-06-06 |
| JPS5516588B2 (de) | 1980-05-02 |
| NL167163C (nl) | 1981-11-16 |
| JPS5511568A (en) | 1980-01-26 |
| FR2387973A1 (fr) | 1978-11-17 |
| NL167163B (nl) | 1981-06-16 |
| IE46411B1 (en) | 1983-06-01 |
| GB1543897A (en) | 1979-04-11 |
| FI773367A (fi) | 1978-05-13 |
| JPS5814434B2 (ja) | 1983-03-18 |
| US4126624A (en) | 1978-11-21 |
| FR2385710A1 (fr) | 1978-10-27 |
| PT67234B (en) | 1979-04-16 |
| DE2750553C2 (de) | 1983-06-30 |
| PT67234A (en) | 1977-12-01 |
| DD134349A5 (de) | 1979-02-21 |
| DE2750553A1 (de) | 1978-05-18 |
| IT1109435B (it) | 1985-12-16 |
| LU78503A1 (fr) | 1979-06-13 |
| ZA776744B (en) | 1978-10-25 |
| BR7707529A (pt) | 1978-06-20 |
| TR19727A (tr) | 1979-11-23 |
| NL7712427A (nl) | 1978-05-17 |
| SE7711964L (sv) | 1978-05-12 |
| DK502077A (da) | 1978-05-13 |
| MX4750E (es) | 1982-08-31 |
| IE772296L (en) | 1978-05-12 |
| AU499476B1 (en) | 1979-04-26 |
| PL202091A1 (pl) | 1979-06-04 |
| FR2385710B1 (de) | 1983-01-07 |
| CA1109478A (en) | 1981-09-22 |
| ES464045A1 (es) | 1978-08-01 |
| BE860699A (fr) | 1978-05-10 |
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