NO743947L - - Google Patents
Info
- Publication number
- NO743947L NO743947L NO743947A NO743947A NO743947L NO 743947 L NO743947 L NO 743947L NO 743947 A NO743947 A NO 743947A NO 743947 A NO743947 A NO 743947A NO 743947 L NO743947 L NO 743947L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- mol
- phenyl
- cyclohexyl
- biphenylyl
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 200
- 239000000203 mixture Substances 0.000 claims description 145
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 120
- 150000001875 compounds Chemical class 0.000 claims description 84
- -1 methyl-substituted cyclohexyl residue Chemical group 0.000 claims description 69
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000002904 solvent Substances 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 239000003054 catalyst Substances 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 150000002576 ketones Chemical class 0.000 claims description 25
- 239000007858 starting material Substances 0.000 claims description 22
- 230000009467 reduction Effects 0.000 claims description 21
- 238000009835 boiling Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 150000001299 aldehydes Chemical class 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 230000002829 reductive effect Effects 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000002902 organometallic compounds Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 230000009471 action Effects 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 150000003333 secondary alcohols Chemical class 0.000 claims description 4
- FYOWZTWVYZOZSI-UHFFFAOYSA-N thiourea dioxide Chemical compound NC(=N)S(O)=O FYOWZTWVYZOZSI-UHFFFAOYSA-N 0.000 claims description 4
- 239000011787 zinc oxide Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 239000010953 base metal Substances 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000003138 primary alcohols Chemical class 0.000 claims description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- HXCKCCRKGXHOBK-UHFFFAOYSA-N cycloheptane Chemical group [CH]1CCCCCC1 HXCKCCRKGXHOBK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 150000002641 lithium Chemical group 0.000 claims description 2
- RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 238000005530 etching Methods 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 379
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 320
- 239000000243 solution Substances 0.000 description 173
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 124
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 114
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 91
- 239000013078 crystal Substances 0.000 description 82
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 76
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 75
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
- 239000000741 silica gel Substances 0.000 description 75
- 229910002027 silica gel Inorganic materials 0.000 description 75
- 229910052938 sodium sulfate Inorganic materials 0.000 description 69
- 235000011152 sodium sulphate Nutrition 0.000 description 69
- 238000002844 melting Methods 0.000 description 66
- 230000008018 melting Effects 0.000 description 66
- 239000003480 eluent Substances 0.000 description 61
- 239000003921 oil Substances 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 55
- 238000003756 stirring Methods 0.000 description 55
- 239000003208 petroleum Substances 0.000 description 52
- 239000010410 layer Substances 0.000 description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 47
- 229960000583 acetic acid Drugs 0.000 description 47
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- 238000001816 cooling Methods 0.000 description 34
- 238000001953 recrystallisation Methods 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 29
- 239000012230 colorless oil Substances 0.000 description 29
- 239000012259 ether extract Substances 0.000 description 29
- 239000000706 filtrate Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 28
- 239000000284 extract Substances 0.000 description 28
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 239000012362 glacial acetic acid Substances 0.000 description 25
- 238000010992 reflux Methods 0.000 description 25
- 235000011121 sodium hydroxide Nutrition 0.000 description 25
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 24
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 24
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 21
- 238000000921 elemental analysis Methods 0.000 description 19
- 238000007254 oxidation reaction Methods 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 230000003647 oxidation Effects 0.000 description 18
- 239000005457 ice water Substances 0.000 description 17
- RLGQKHIVWSMQHD-UHFFFAOYSA-N 4-(3-chloro-4-cyclohexylphenyl)pentan-2-one Chemical group ClC1=CC(C(CC(C)=O)C)=CC=C1C1CCCCC1 RLGQKHIVWSMQHD-UHFFFAOYSA-N 0.000 description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- 239000008346 aqueous phase Substances 0.000 description 16
- 239000012279 sodium borohydride Substances 0.000 description 16
- 229910000033 sodium borohydride Inorganic materials 0.000 description 16
- 238000001228 spectrum Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 15
- 239000011777 magnesium Substances 0.000 description 15
- 229910052749 magnesium Inorganic materials 0.000 description 15
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 14
- 206010030113 Oedema Diseases 0.000 description 14
- ZOCYCSPSSNMXBU-VOTSOKGWSA-N ethyl (e)-3-ethoxybut-2-enoate Chemical compound CCO\C(C)=C\C(=O)OCC ZOCYCSPSSNMXBU-VOTSOKGWSA-N 0.000 description 14
- 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 13
- 238000010521 absorption reaction Methods 0.000 description 13
- 239000001569 carbon dioxide Substances 0.000 description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 11
- ZFPXAHIIBAESLM-UHFFFAOYSA-N 4-(3-chloro-4-cyclohexylphenyl)pentan-2-ol Chemical compound ClC1=CC(C(C)CC(O)C)=CC=C1C1CCCCC1 ZFPXAHIIBAESLM-UHFFFAOYSA-N 0.000 description 11
- IDGLDZNDBFSUAC-UHFFFAOYSA-N 4-(4-cyclohexylphenyl)pentan-2-one Chemical compound C1=CC(C(CC(C)=O)C)=CC=C1C1CCCCC1 IDGLDZNDBFSUAC-UHFFFAOYSA-N 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
- FDPQJAXXWIIWLN-VOTSOKGWSA-N (e)-4-[4-(2-fluorophenyl)phenyl]but-3-en-2-one Chemical compound C1=CC(/C=C/C(=O)C)=CC=C1C1=CC=CC=C1F FDPQJAXXWIIWLN-VOTSOKGWSA-N 0.000 description 10
- 239000007818 Grignard reagent Substances 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 239000007868 Raney catalyst Substances 0.000 description 10
- 229910000564 Raney nickel Inorganic materials 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 150000004795 grignard reagents Chemical class 0.000 description 10
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- MQWZPJXOCQPUHR-BQYQJAHWSA-N (e)-4-(3-fluoro-4-phenylphenyl)but-3-en-2-one Chemical compound FC1=CC(/C=C/C(=O)C)=CC=C1C1=CC=CC=C1 MQWZPJXOCQPUHR-BQYQJAHWSA-N 0.000 description 8
- SJOJOQISYXPHEL-OUKQBFOZSA-N (e)-4-(4-cyclohexylphenyl)pent-3-en-2-one Chemical compound C1=CC(C(/C)=C/C(=O)C)=CC=C1C1CCCCC1 SJOJOQISYXPHEL-OUKQBFOZSA-N 0.000 description 8
- JQCXEFJAWHZRAH-UHFFFAOYSA-N 4-(4-cyclohexylphenyl)pentan-2-ol Chemical compound C1=CC(C(C)CC(O)C)=CC=C1C1CCCCC1 JQCXEFJAWHZRAH-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 238000011097 chromatography purification Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 7
- SJDSKTZJLMIJML-UHFFFAOYSA-N 4-(3-fluoro-4-phenylphenyl)butan-2-one Chemical compound FC1=CC(CCC(=O)C)=CC=C1C1=CC=CC=C1 SJDSKTZJLMIJML-UHFFFAOYSA-N 0.000 description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 7
- NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 229910052725 zinc Inorganic materials 0.000 description 7
- 239000011701 zinc Substances 0.000 description 7
- CPMNCPJGQAMUGN-UHFFFAOYSA-N 3-chloro-4-cyclohexylbenzaldehyde Chemical compound ClC1=CC(C=O)=CC=C1C1CCCCC1 CPMNCPJGQAMUGN-UHFFFAOYSA-N 0.000 description 6
- LQNYROAMULRPKI-UHFFFAOYSA-N 4-(3-fluoro-4-phenylphenyl)butan-2-ol Chemical compound FC1=CC(CCC(O)C)=CC=C1C1=CC=CC=C1 LQNYROAMULRPKI-UHFFFAOYSA-N 0.000 description 6
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- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- YHOBGCSGTGDMLF-UHFFFAOYSA-N sodium;di(propan-2-yl)azanide Chemical compound [Na+].CC(C)[N-]C(C)C YHOBGCSGTGDMLF-UHFFFAOYSA-N 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229910003452 thorium oxide Inorganic materials 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
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- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
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- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE2362589A DE2362589A1 (de) | 1973-12-17 | 1973-12-17 | Neue araliphatische ketone und carbinole und verfahren zu ihrer herstellung |
DE19742450991 DE2450991A1 (de) | 1974-10-26 | 1974-10-26 | Neue araliphatische ketone und carbinole, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
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NO743947L true NO743947L (es) | 1975-07-14 |
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JP (1) | JPS5093932A (es) |
AT (1) | ATA937274A (es) |
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DD (1) | DD118270A5 (es) |
DK (1) | DK655274A (es) |
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FI (1) | FI357774A (es) |
FR (1) | FR2254320B1 (es) |
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IL (1) | IL46252A0 (es) |
NL (1) | NL7416340A (es) |
NO (1) | NO743947L (es) |
PH (1) | PH12536A (es) |
RO (4) | RO66030A (es) |
SE (1) | SE7415796L (es) |
Families Citing this family (16)
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BE724125A (fr) * | 1968-11-19 | 1969-05-19 | Acec | Dispositif de commande de position |
US3557223A (en) * | 1969-03-14 | 1971-01-19 | Engelhard Min & Chem | Hydrogenation of aralkyl ketones |
NL7414790A (nl) * | 1973-08-20 | 1976-05-17 | Sandoz Ag | Werkwijzen voor het bereiden van een aromatische verbinding en van therapeutische preparaten die een of een aantal van deze verbindingen bevat- ten. |
US4344966A (en) * | 1973-08-20 | 1982-08-17 | Sandoz, Inc. | Anti-inflammatory 1-alkyl-1-phenyl-butanes |
GB1479297A (en) * | 1974-07-04 | 1977-07-13 | Beecham Group Ltd | 4-substituted butan-2-ones but-3-en-2-ones butan-2-ols and but-3-en-2-ols and pharmaceutical compositions containing them |
US4567279A (en) * | 1984-12-13 | 1986-01-28 | Usv Pharmaceutical Corp. | Diarylhydroxy alkanones and alkenones antiallergy agents |
NL8801908A (nl) * | 1988-07-29 | 1990-02-16 | Shell Int Research | Bereiding van polymere polyalcoholen. |
FR2632978B1 (fr) * | 1988-06-17 | 1990-09-28 | Poudres & Explosifs Ste Nale | Procede d'electrosynthese de carbinols benzyliques |
US5286895A (en) * | 1992-02-19 | 1994-02-15 | Merck & Co., Inc. | Cholesterol lowering compounds |
TW348175B (en) * | 1993-01-06 | 1998-12-21 | Hoechst Ag | Process for the preparation of biphenyl derivatives |
FR2711367B1 (fr) * | 1993-10-19 | 1995-12-01 | Roussel Uclaf | Nouveau procédé de préparation de dérivés soufrés de l'imidazole et les nouveaux intermédiaires obtenus. |
DE102004055189B4 (de) * | 2004-11-16 | 2007-02-08 | Süd-Chemie AG | Verfahren zur Hydrierung von Acetophenon |
US9090604B2 (en) | 2006-07-27 | 2015-07-28 | E I Du Pont De Nemours And Company | Fungicidal azocyclic amides |
WO2008013622A2 (en) * | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
US8357635B2 (en) | 2009-10-16 | 2013-01-22 | Syngenta Crop Protection Llc | Microbiocides |
BR112015007937A2 (pt) | 2012-10-12 | 2017-07-04 | Bristol Myers Squibb Co | formas cristalinas de um inibidor de fator xia |
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---|---|---|---|---|
US3702343A (en) * | 1969-08-11 | 1972-11-07 | Int Flavors & Fragrances Inc | 2-methyl-2-(tertiary alkyl cyclohexyl) pentan-4-ones and processes |
DE2240440A1 (de) * | 1972-08-17 | 1974-02-28 | Thomae Gmbh Dr K | Neue (4-biphenylyl)-alkohole und verfahren zu ihrer herstellung |
US3879449A (en) * | 1974-03-04 | 1975-04-22 | Sandoz Ag | 1-Phenyl-4-hydroxy-1-buten-3-ones and esters thereof |
-
1974
- 1974-11-22 AT AT937274A patent/ATA937274A/de not_active Application Discontinuation
- 1974-12-09 RO RO7473777A patent/RO66030A/ro unknown
- 1974-12-09 RO RO7483782A patent/RO68187A/ro unknown
- 1974-12-09 RO RO7483779A patent/RO66157A/ro unknown
- 1974-12-09 RO RO7480732A patent/RO67288A/ro unknown
- 1974-12-10 BG BG7428415A patent/BG26363A3/xx unknown
- 1974-12-11 NO NO743947A patent/NO743947L/no unknown
- 1974-12-11 ES ES432786A patent/ES432786A1/es not_active Expired
- 1974-12-12 FI FI3577/74A patent/FI357774A/fi unknown
- 1974-12-12 US US05/532,174 patent/US3950427A/en not_active Expired - Lifetime
- 1974-12-16 HU HUTO991A patent/HU168459B/hu unknown
- 1974-12-16 JP JP49144353A patent/JPS5093932A/ja active Pending
- 1974-12-16 NL NL7416340A patent/NL7416340A/xx not_active Application Discontinuation
- 1974-12-16 SE SE7415796A patent/SE7415796L/xx unknown
- 1974-12-16 DK DK655274A patent/DK655274A/da not_active Application Discontinuation
- 1974-12-16 IL IL46252A patent/IL46252A0/xx unknown
- 1974-12-17 GB GB54467/74A patent/GB1497857A/en not_active Expired
- 1974-12-17 DD DD183111A patent/DD118270A5/xx unknown
- 1974-12-17 PH PH16636A patent/PH12536A/en unknown
- 1974-12-17 IE IE2605/74A patent/IE42212B1/en unknown
- 1974-12-17 FR FR7441524A patent/FR2254320B1/fr not_active Expired
-
1976
- 1976-10-05 ES ES452104A patent/ES452104A1/es not_active Expired
- 1976-10-05 ES ES452109A patent/ES452109A1/es not_active Expired
- 1976-10-05 ES ES452113A patent/ES452113A1/es not_active Expired
- 1976-10-05 ES ES452111A patent/ES452111A1/es not_active Expired
- 1976-10-05 ES ES452110A patent/ES452110A1/es not_active Expired
- 1976-10-05 ES ES452108A patent/ES452108A1/es not_active Expired
- 1976-10-05 ES ES452107A patent/ES452107A1/es not_active Expired
- 1976-10-05 ES ES452106A patent/ES452106A1/es not_active Expired
- 1976-10-05 ES ES452112A patent/ES452112A1/es not_active Expired
- 1976-10-05 ES ES452105A patent/ES452105A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
RO68187A (ro) | 1980-08-15 |
IE42212B1 (en) | 1980-07-02 |
ES452111A1 (es) | 1977-10-01 |
ES452110A1 (es) | 1977-10-01 |
DD118270A5 (es) | 1976-02-20 |
HU168459B (es) | 1976-04-28 |
IE42212L (en) | 1975-06-17 |
ES452105A1 (es) | 1977-10-01 |
GB1497857A (en) | 1978-01-12 |
IL46252A0 (en) | 1975-03-13 |
PH12536A (en) | 1979-05-17 |
FR2254320A1 (es) | 1975-07-11 |
ATA937274A (de) | 1978-02-15 |
FI357774A (es) | 1975-06-18 |
JPS5093932A (es) | 1975-07-26 |
ES452113A1 (es) | 1977-10-01 |
RO67288A (ro) | 1980-01-15 |
FR2254320B1 (es) | 1978-08-18 |
ES452112A1 (es) | 1977-10-01 |
ES452106A1 (es) | 1977-10-01 |
ES452104A1 (es) | 1977-10-16 |
DK655274A (es) | 1975-08-25 |
US3950427A (en) | 1976-04-13 |
ES452108A1 (es) | 1977-10-01 |
RO66157A (ro) | 1980-07-15 |
BG26363A3 (es) | 1979-03-15 |
RO66030A (ro) | 1980-06-15 |
AU7645074A (en) | 1976-06-17 |
ES452109A1 (es) | 1977-10-01 |
NL7416340A (nl) | 1975-06-19 |
ES452107A1 (es) | 1977-10-01 |
ES432786A1 (es) | 1977-02-16 |
SE7415796L (es) | 1975-06-18 |
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