HU190824B - Process for resolving alkohols and semiacetals - Google Patents
Process for resolving alkohols and semiacetals Download PDFInfo
- Publication number
- HU190824B HU190824B HU823957A HU395782A HU190824B HU 190824 B HU190824 B HU 190824B HU 823957 A HU823957 A HU 823957A HU 395782 A HU395782 A HU 395782A HU 190824 B HU190824 B HU 190824B
- Authority
- HU
- Hungary
- Prior art keywords
- product
- formula
- cyano
- mixture
- dimethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 9
- 238000004587 chromatography analysis Methods 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 229910052801 chlorine Chemical group 0.000 abstract description 2
- 239000000460 chlorine Chemical group 0.000 abstract description 2
- 125000002950 monocyclic group Chemical group 0.000 abstract description 2
- 125000003367 polycyclic group Chemical group 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001976 hemiacetal group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 107
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 92
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 87
- 239000000203 mixture Substances 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- -1 cyanomethyl Chemical group 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 239000000741 silica gel Substances 0.000 description 25
- 229910002027 silica gel Inorganic materials 0.000 description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 239000012074 organic phase Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 238000010828 elution Methods 0.000 description 16
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
- RRYCIULTIFONEQ-UHFFFAOYSA-N naphtho[2,3-e][1]benzofuran Chemical compound C1=CC=C2C=C3C(C=CO4)=C4C=CC3=CC2=C1 RRYCIULTIFONEQ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 0 CC(*)c1ccccc1 Chemical compound CC(*)c1ccccc1 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- GXUQMKBQDGPMKZ-CQSZACIVSA-N (2s)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#C[C@@H](O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-CQSZACIVSA-N 0.000 description 5
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- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002178 crystalline material Substances 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 238000010908 decantation Methods 0.000 description 5
- IJFQNCSYGCGEBS-ZLUOBGJFSA-N (1r,2s,5s)-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-ol Chemical compound C1O[C@H](O)[C@H]2C(C)(C)[C@H]21 IJFQNCSYGCGEBS-ZLUOBGJFSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000002983 circular dichroism Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JCKXRFUNQXHNKX-MOJAZDJTSA-N (1r,2s,4r,5s)-6,6-dimethyl-4-(trichloromethyl)-3-oxabicyclo[3.1.0]hexan-2-ol Chemical compound [C@@H]1([C@H](O[C@H]2C(Cl)(Cl)Cl)O)[C@H]2C1(C)C JCKXRFUNQXHNKX-MOJAZDJTSA-N 0.000 description 2
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- FYMRFGOANQSOAR-UHFFFAOYSA-N COC1OCC2C1C1c3ccccc3C11c3ccccc3C21 Chemical compound COC1OCC2C1C1c3ccccc3C11c3ccccc3C21 FYMRFGOANQSOAR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ICGWWCLWBPLPDF-UHFFFAOYSA-N furan-2-ol Chemical compound OC1=CC=CO1 ICGWWCLWBPLPDF-UHFFFAOYSA-N 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- SERHXTVXHNVDKA-UHFFFAOYSA-N pantolactone Chemical compound CC1(C)COC(=O)C1O SERHXTVXHNVDKA-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
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
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- 239000001476 sodium potassium tartrate Substances 0.000 description 2
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 2
- 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 2
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- GERXDGZUFWGVCC-UHFFFAOYSA-N 1-hydroxyimidazolidine-2,4-dione Chemical compound ON1CC(=O)NC1=O GERXDGZUFWGVCC-UHFFFAOYSA-N 0.000 description 1
- NUWVRSQLOXLCEM-UHFFFAOYSA-N 4-oxatricyclo[4.2.1.03,7]nonan-5-ol Chemical compound C1C2C(O)OC3C2CC1C3 NUWVRSQLOXLCEM-UHFFFAOYSA-N 0.000 description 1
- DUAZKLYNTLDKQK-UHFFFAOYSA-N 5-hydroxy-2(5h)-furanone Chemical compound OC1OC(=O)C=C1 DUAZKLYNTLDKQK-UHFFFAOYSA-N 0.000 description 1
- ZVTOOXJEFHQAKK-UHFFFAOYSA-N 5-hydroxy-4-oxatricyclo[5.2.1.02,6]deca-1(9),7-dien-3-one Chemical compound C1=C(C2)C3C(=O)OC(O)C3C2=C1 ZVTOOXJEFHQAKK-UHFFFAOYSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
- IJFQNCSYGCGEBS-UHFFFAOYSA-N 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-ol Chemical compound C1OC(O)C2C(C)(C)C21 IJFQNCSYGCGEBS-UHFFFAOYSA-N 0.000 description 1
- ZFCNOHNDCYYXIK-UHFFFAOYSA-N 6-bromohexahydro-2h-3,5-methanocyclopenta[b]furan-2-one Chemical compound O=C1OC2C(Br)C3CC1C2C3 ZFCNOHNDCYYXIK-UHFFFAOYSA-N 0.000 description 1
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PHLNUALMSJMNHN-UHFFFAOYSA-N CC(C1CCCCC1)OC(C12)OCC1C1C3=CCCC=C3C2c2ccccc12 Chemical compound CC(C1CCCCC1)OC(C12)OCC1C1C3=CCCC=C3C2c2ccccc12 PHLNUALMSJMNHN-UHFFFAOYSA-N 0.000 description 1
- JIQRGPPACWMYDF-ZGXWSNOMSA-N CC1([C@H]2CO[C@@H]([C@@H]12)O[C@@H](C1=CC(=CC=C1)OC1=CC=CC=C1)C#N)C Chemical compound CC1([C@H]2CO[C@@H]([C@@H]12)O[C@@H](C1=CC(=CC=C1)OC1=CC=CC=C1)C#N)C JIQRGPPACWMYDF-ZGXWSNOMSA-N 0.000 description 1
- XJLZYZQEHKOPKT-QNDJGXFYSA-N CC1([C@H]2CO[C@@H]([C@@H]12)O[C@@H](C1=NC(=CC=C1)OC1=CC=CC=C1)C#N)C Chemical compound CC1([C@H]2CO[C@@H]([C@@H]12)O[C@@H](C1=NC(=CC=C1)OC1=CC=CC=C1)C#N)C XJLZYZQEHKOPKT-QNDJGXFYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- HUQDNWIWIQCBEA-UHFFFAOYSA-N OC(C12)OC=C1C1c3ccccc3C2c2c1cccc2 Chemical compound OC(C12)OC=C1C1c3ccccc3C2c2c1cccc2 HUQDNWIWIQCBEA-UHFFFAOYSA-N 0.000 description 1
- VMQOBKMYELKRQK-UHFFFAOYSA-N OC(C1C2c3ccccc3C22)OCC1C2=C1C=CCC=C1 Chemical compound OC(C1C2c3ccccc3C22)OCC1C2=C1C=CCC=C1 VMQOBKMYELKRQK-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- GBGSMFSPTNKMIT-UHFFFAOYSA-N anthracene furan Chemical compound C=1C=COC=1.C1=CC=CC2=CC3=CC=CC=C3C=C21 GBGSMFSPTNKMIT-UHFFFAOYSA-N 0.000 description 1
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- WKOARXCZOFTJEB-UHFFFAOYSA-N hexahydro-2h-3,5-methanocyclopenta[b]furan Chemical compound C1C2COC3C2CC1C3 WKOARXCZOFTJEB-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octane-2-ol Natural products CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- AVTYONGGKAJVTE-OLXYHTOASA-L potassium L-tartrate Chemical compound [K+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O AVTYONGGKAJVTE-OLXYHTOASA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- 229940111695 potassium tartrate Drugs 0.000 description 1
- 235000011005 potassium tartrates Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/02—Saturated compounds containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8123003A FR2517677B1 (fr) | 1981-12-09 | 1981-12-09 | Nouveaux ethers dont les restes organiques comportent des atomes chiraux, leur procede de preparation et leur application au dedoublement des alcools ou de certains composes de structure hemiacetalique. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU190824B true HU190824B (en) | 1986-11-28 |
Family
ID=9264827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU823957A HU190824B (en) | 1981-12-09 | 1982-12-08 | Process for resolving alkohols and semiacetals |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US4701542A (en, 2012) |
| EP (1) | EP0082049B1 (en, 2012) |
| JP (1) | JPS58105979A (en, 2012) |
| AT (1) | ATE28640T1 (en, 2012) |
| AU (1) | AU560203B2 (en, 2012) |
| CA (1) | CA1238331A (en, 2012) |
| DD (1) | DD203717A5 (en, 2012) |
| DE (1) | DE3276860D1 (en, 2012) |
| DK (1) | DK539182A (en, 2012) |
| ES (1) | ES8308555A1 (en, 2012) |
| FR (1) | FR2517677B1 (en, 2012) |
| HU (1) | HU190824B (en, 2012) |
| IE (1) | IE54308B1 (en, 2012) |
| IL (1) | IL67387A (en, 2012) |
| PT (1) | PT75953B (en, 2012) |
| ZA (1) | ZA828911B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2517677B1 (fr) * | 1981-12-09 | 1986-05-16 | Roussel Uclaf | Nouveaux ethers dont les restes organiques comportent des atomes chiraux, leur procede de preparation et leur application au dedoublement des alcools ou de certains composes de structure hemiacetalique. |
| IN162785B (en, 2012) * | 1984-09-28 | 1988-07-09 | Indian Explosives Ltd | |
| US5015550A (en) * | 1985-10-30 | 1991-05-14 | Xerox Corporation | Electrophotographic coated carrier particles and methods thereof |
| DE3904496A1 (de) * | 1989-02-15 | 1990-08-16 | Merck Patent Gmbh | Verfahren zur enantiomerentrennung eines benzopyranderivats |
| GB8911080D0 (en) * | 1989-05-15 | 1989-06-28 | Merck Sharp & Dohme | Chemical process |
| US5246012A (en) | 1990-12-21 | 1993-09-21 | Ballard Medical Products | Bronchoalveolar lavage catheter |
| AT396686B (de) * | 1992-04-13 | 1993-11-25 | Christian Dr Noe | Reagention zur razemattrennung, verfahren zu ihrer herstellung und verwendung |
| DE60019239T3 (de) * | 1999-12-09 | 2017-03-02 | Dsm Ip Assets B.V. | Fettlösliche Vitamine enthaltende Zusammensetzungen |
| DE102007013262A1 (de) * | 2007-03-15 | 2008-09-18 | Basf Coatings Ag | Beschichtungsmittel enthaltend Addukte mit Silanfunktionalität und daraus hergestellte hochkratzfeste Beschichtungen mit verbesserter Rissbeständigkeit |
| DE102007013242A1 (de) * | 2007-03-15 | 2008-09-18 | Basf Coatings Ag | Hochkratzfeste Beschichtung mit guter Witterungs- und Rissbeständigkeit |
| JP2009091303A (ja) * | 2007-10-10 | 2009-04-30 | Sumitomo Chemical Co Ltd | ６，６−ジメチル−３−オキサビシクロ［３．１．０］ヘキサン−２−オンの製造方法 |
| US8746395B2 (en) | 2012-05-17 | 2014-06-10 | Caterpillar Inc. | Operator interface for machine control |
| USD980663S1 (en) * | 2021-07-29 | 2023-03-14 | Sodastream Industries Ltd. | Domestic soda-water preparing device |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2709264C3 (de) * | 1977-03-03 | 1982-01-21 | Bayer Ag, 5090 Leverkusen | Substituierte Phenoxybenzyloxycarbonylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide sowie neue Zwischenprodukte |
| US4163787A (en) * | 1977-03-14 | 1979-08-07 | The Dow Chemical Company | Substituted pyridine methyl esters of cyclopropane carboxylic acids and their use as insecticides |
| FR2423488A1 (fr) * | 1978-03-17 | 1979-11-16 | Roussel Uclaf | Nouveaux ethers dont les restes organiques comportent des atomes chiraux, leur procede de preparation et leur application au dedoublement des alcools, des phenols ou de certains composes de structure lactonique |
| FR2482955A1 (fr) * | 1980-05-23 | 1981-11-27 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites |
| FR2517677B1 (fr) * | 1981-12-09 | 1986-05-16 | Roussel Uclaf | Nouveaux ethers dont les restes organiques comportent des atomes chiraux, leur procede de preparation et leur application au dedoublement des alcools ou de certains composes de structure hemiacetalique. |
| US4497960A (en) * | 1981-12-18 | 1985-02-05 | Christian Noe | Chiral, optically active compounds useful as protective groups for hydroxy, thiol and amino compounds |
-
1981
- 1981-12-09 FR FR8123003A patent/FR2517677B1/fr not_active Expired
-
1982
- 1982-12-01 IL IL6738782A patent/IL67387A/en not_active IP Right Cessation
- 1982-12-03 ZA ZA828911A patent/ZA828911B/xx unknown
- 1982-12-03 DE DE8282402211T patent/DE3276860D1/de not_active Expired
- 1982-12-03 EP EP82402211A patent/EP0082049B1/fr not_active Expired
- 1982-12-03 AT AT82402211T patent/ATE28640T1/de not_active IP Right Cessation
- 1982-12-06 DK DK539182A patent/DK539182A/da not_active Application Discontinuation
- 1982-12-07 ES ES517981A patent/ES8308555A1/es not_active Expired
- 1982-12-07 PT PT75953A patent/PT75953B/pt not_active IP Right Cessation
- 1982-12-08 DD DD82245706A patent/DD203717A5/de not_active IP Right Cessation
- 1982-12-08 IE IE2922/82A patent/IE54308B1/en not_active IP Right Cessation
- 1982-12-08 HU HU823957A patent/HU190824B/hu not_active IP Right Cessation
- 1982-12-08 CA CA000417233A patent/CA1238331A/fr not_active Expired
- 1982-12-09 AU AU91363/82A patent/AU560203B2/en not_active Ceased
- 1982-12-09 JP JP57214738A patent/JPS58105979A/ja active Granted
-
1986
- 1986-03-31 US US06/846,570 patent/US4701542A/en not_active Expired - Fee Related
-
1987
- 1987-07-17 US US07/074,682 patent/US4788305A/en not_active Expired - Fee Related
-
1988
- 1988-05-25 US US07/198,482 patent/US4935532A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IL67387A (en) | 1994-07-31 |
| US4935532A (en) | 1990-06-19 |
| PT75953A (fr) | 1983-01-01 |
| EP0082049B1 (fr) | 1987-07-29 |
| AU560203B2 (en) | 1987-04-02 |
| FR2517677A1 (fr) | 1983-06-10 |
| IE54308B1 (en) | 1989-08-16 |
| PT75953B (fr) | 1985-12-20 |
| CA1238331A (fr) | 1988-06-21 |
| US4701542A (en) | 1987-10-20 |
| DE3276860D1 (en) | 1987-09-03 |
| DK539182A (da) | 1983-06-10 |
| EP0082049A2 (fr) | 1983-06-22 |
| DD203717A5 (de) | 1983-11-02 |
| JPS58105979A (ja) | 1983-06-24 |
| EP0082049A3 (en) | 1983-11-09 |
| IL67387A0 (en) | 1983-05-15 |
| AU9136382A (en) | 1983-06-16 |
| ES517981A0 (es) | 1983-09-01 |
| ZA828911B (en) | 1984-01-25 |
| FR2517677B1 (fr) | 1986-05-16 |
| US4788305A (en) | 1988-11-29 |
| ATE28640T1 (de) | 1987-08-15 |
| IE822922L (en) | 1983-06-09 |
| ES8308555A1 (es) | 1983-09-01 |
| JPH0372064B2 (en, 2012) | 1991-11-15 |
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| HMM4 | Cancellation of final prot. due to non-payment of fee |