FI61026C - Foerfarande foer framstaellning av alfa-etynyl-benshydroler - Google Patents
Foerfarande foer framstaellning av alfa-etynyl-benshydroler Download PDFInfo
- Publication number
- FI61026C FI61026C FI2400/74A FI240074A FI61026C FI 61026 C FI61026 C FI 61026C FI 2400/74 A FI2400/74 A FI 2400/74A FI 240074 A FI240074 A FI 240074A FI 61026 C FI61026 C FI 61026C
- Authority
- FI
- Finland
- Prior art keywords
- acetylene
- potassium
- minutes
- reaction mixture
- ethynyl
- Prior art date
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- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 65
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000012965 benzophenone Substances 0.000 claims description 24
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000000010 aprotic solvent Substances 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 239000011541 reaction mixture Substances 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 238000002474 experimental method Methods 0.000 description 31
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- 238000004458 analytical method Methods 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 24
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 238000003756 stirring Methods 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000008366 benzophenones Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- -1 ethynylene magnesium bromide Chemical compound 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229940035429 isobutyl alcohol Drugs 0.000 description 6
- CBMSDILKECEMOT-UHFFFAOYSA-N potassium;2-methylpropan-1-olate Chemical compound [K+].CC(C)C[O-] CBMSDILKECEMOT-UHFFFAOYSA-N 0.000 description 6
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000006203 ethylation Effects 0.000 description 3
- 238000006200 ethylation reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- SMCLTAARQYTXLW-UHFFFAOYSA-N 1,1-diphenylprop-2-yn-1-ol Chemical compound C=1C=CC=CC=1C(C#C)(O)C1=CC=CC=C1 SMCLTAARQYTXLW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DWFDQVMFSLLMPE-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC=CC=C1 DWFDQVMFSLLMPE-UHFFFAOYSA-N 0.000 description 1
- CSUUDNFYSFENAE-UHFFFAOYSA-N (2-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=CC=C1 CSUUDNFYSFENAE-UHFFFAOYSA-N 0.000 description 1
- NBBLWZCKRCFVRM-UHFFFAOYSA-N (2-tert-butylphenyl)-phenylmethanone Chemical compound CC(C)(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NBBLWZCKRCFVRM-UHFFFAOYSA-N 0.000 description 1
- CPLWKNRPZVNELG-UHFFFAOYSA-N (3-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 CPLWKNRPZVNELG-UHFFFAOYSA-N 0.000 description 1
- BYFTYMVRQNYFJD-UHFFFAOYSA-N (3-ethynylphenyl)-phenylmethanol Chemical compound C=1C=CC(C#C)=CC=1C(O)C1=CC=CC=C1 BYFTYMVRQNYFJD-UHFFFAOYSA-N 0.000 description 1
- JAFDVXCJWWEVND-UHFFFAOYSA-N (3-iodophenyl)-phenylmethanone Chemical compound IC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 JAFDVXCJWWEVND-UHFFFAOYSA-N 0.000 description 1
- YLQAYDRTBZGIPG-UHFFFAOYSA-N (6,6-dichlorocyclohexa-2,4-dien-1-yl)-phenylmethanone Chemical compound ClC1(Cl)C=CC=CC1C(=O)C1=CC=CC=C1 YLQAYDRTBZGIPG-UHFFFAOYSA-N 0.000 description 1
- ILUUADPFGUWLMN-UHFFFAOYSA-N (6-ethynyl-6-fluorocyclohexa-2,4-dien-1-yl)-phenylmethanol Chemical compound FC1(C(C(C2=CC=CC=C2)O)C=CC=C1)C#C ILUUADPFGUWLMN-UHFFFAOYSA-N 0.000 description 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- QNPRBAHAXCXLKI-UHFFFAOYSA-N C#CC1=C(C=C(C=C1)C(C2=CC=CC=C2)O)C(F)(F)F Chemical compound C#CC1=C(C=C(C=C1)C(C2=CC=CC=C2)O)C(F)(F)F QNPRBAHAXCXLKI-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZHWKDURAWFJFBE-UHFFFAOYSA-N ClC=1C=CC=C(C(=O)C2=C(C=CC=C2)NC(C2=CC=CC=C2)=O)C=1 Chemical compound ClC=1C=CC=C(C(=O)C2=C(C=CC=C2)NC(C2=CC=CC=C2)=O)C=1 ZHWKDURAWFJFBE-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NDFRQASCTNSTFY-UHFFFAOYSA-N N-[4-chloro-1-ethynyl-6-[hydroxy(phenyl)methyl]cyclohexa-2,4-dien-1-yl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1(C(C(C2=CC=CC=C2)O)C=C(C=C1)Cl)C#C NDFRQASCTNSTFY-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FONLFYJMMLWRFE-UHFFFAOYSA-N [4-(bromomethyl)phenyl]-phenylmethanol Chemical compound C1=CC=CC(=C1)C(O)C1=CC=C(CBr)C=C1 FONLFYJMMLWRFE-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000531 effect on virus Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- IUXBGCZGJQVUBJ-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=C1 IUXBGCZGJQVUBJ-UHFFFAOYSA-N 0.000 description 1
- UALVNMHTCDKVQA-UHFFFAOYSA-N n-[4-chloro-2-(1-hydroxy-1-phenylprop-2-ynyl)phenyl]benzamide Chemical compound C=1C(Cl)=CC=C(NC(=O)C=2C=CC=CC=2)C=1C(C#C)(O)C1=CC=CC=C1 UALVNMHTCDKVQA-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- IOXDAYKKVHAKSX-UHFFFAOYSA-N phenyl-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 IOXDAYKKVHAKSX-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—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
- C07C29/38—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
- C07C29/42—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 triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/28—Alcohols containing only six-membered aromatic rings as cyclic part with unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
- C07C33/486—Polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HURI000520 | 1973-08-15 | ||
HURI520A HU166769B (cs) | 1973-08-15 | 1973-08-15 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI240074A7 FI240074A7 (cs) | 1975-02-16 |
FI61026B FI61026B (fi) | 1982-01-29 |
FI61026C true FI61026C (fi) | 1982-05-10 |
Family
ID=11000931
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI2400/74A FI61026C (fi) | 1973-08-15 | 1974-08-13 | Foerfarande foer framstaellning av alfa-etynyl-benshydroler |
Country Status (21)
Country | Link |
---|---|
US (1) | US3965179A (cs) |
JP (1) | JPS525506B2 (cs) |
AT (1) | AT338763B (cs) |
AU (1) | AU484223B2 (cs) |
BE (1) | BE818796A (cs) |
BG (1) | BG21011A3 (cs) |
CA (1) | CA1039309A (cs) |
CS (1) | CS189663B2 (cs) |
DD (1) | DD113743A5 (cs) |
DE (1) | DE2438462C3 (cs) |
DK (1) | DK433474A (cs) |
ES (1) | ES429276A1 (cs) |
FI (1) | FI61026C (cs) |
FR (1) | FR2240724B1 (cs) |
GB (1) | GB1445531A (cs) |
HU (1) | HU166769B (cs) |
IL (1) | IL45390A (cs) |
NL (1) | NL7410634A (cs) |
RO (2) | RO76175A (cs) |
SE (1) | SE402583B (cs) |
SU (1) | SU689613A3 (cs) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1985004394A1 (en) * | 1984-03-26 | 1985-10-10 | Kyowa Hakko Kogyo Co. Ltd. | Alkynol compounds and alcohol separating agents |
CN101495245A (zh) | 2005-04-15 | 2009-07-29 | 利·H·安格罗斯 | 分析基板涂覆装置和方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2996552A (en) * | 1958-10-28 | 1961-08-15 | Air Reduction | Preparation of acetylenic alcohols |
US3494961A (en) * | 1965-03-12 | 1970-02-10 | Hoffmann La Roche | 1,4-bis-(p-(dialkylaminoalkoxy)aryl)-1,4-bis-(aryl)-2-b-1,4-diols |
GB1129955A (en) * | 1966-03-03 | 1968-10-09 | Wyeth John & Brother Ltd | Unsaturated nitriles and esters and derivatives thereof |
US3663628A (en) * | 1970-07-06 | 1972-05-16 | Air Prod & Chem | Catalysts for producing acetylenic alcohols |
-
1973
- 1973-08-15 HU HURI520A patent/HU166769B/hu unknown
-
1974
- 1974-07-31 AT AT627574A patent/AT338763B/de not_active IP Right Cessation
- 1974-08-02 AU AU71967/74A patent/AU484223B2/en not_active Expired
- 1974-08-02 IL IL45390A patent/IL45390A/xx unknown
- 1974-08-07 NL NL7410634A patent/NL7410634A/xx not_active Application Discontinuation
- 1974-08-08 US US05/495,846 patent/US3965179A/en not_active Expired - Lifetime
- 1974-08-09 SE SE7410242A patent/SE402583B/xx unknown
- 1974-08-09 DE DE2438462A patent/DE2438462C3/de not_active Expired
- 1974-08-10 BG BG027472A patent/BG21011A3/xx unknown
- 1974-08-12 GB GB3538574A patent/GB1445531A/en not_active Expired
- 1974-08-13 RO RO7496830A patent/RO76175A/ro unknown
- 1974-08-13 CS CS745675A patent/CS189663B2/cs unknown
- 1974-08-13 FI FI2400/74A patent/FI61026C/fi active
- 1974-08-13 BE BE147563A patent/BE818796A/xx not_active IP Right Cessation
- 1974-08-13 FR FR7428084A patent/FR2240724B1/fr not_active Expired
- 1974-08-13 RO RO7479756A patent/RO70575A/ro unknown
- 1974-08-13 DD DD180469A patent/DD113743A5/xx unknown
- 1974-08-14 SU SU742055570A patent/SU689613A3/ru active
- 1974-08-14 DK DK433474A patent/DK433474A/da not_active Application Discontinuation
- 1974-08-14 CA CA207,026A patent/CA1039309A/en not_active Expired
- 1974-08-14 ES ES429276A patent/ES429276A1/es not_active Expired
- 1974-08-15 JP JP49092892A patent/JPS525506B2/ja not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FI61026B (fi) | 1982-01-29 |
DE2438462A1 (de) | 1975-02-27 |
RO70575A (ro) | 1982-09-09 |
DE2438462C3 (de) | 1978-08-03 |
IL45390A0 (en) | 1974-11-29 |
HU166769B (cs) | 1975-05-28 |
DE2438462B2 (de) | 1977-12-01 |
US3965179A (en) | 1976-06-22 |
FR2240724A1 (cs) | 1975-03-14 |
DK433474A (cs) | 1975-04-28 |
IL45390A (en) | 1978-06-15 |
DD113743A5 (cs) | 1975-06-20 |
AU7196774A (en) | 1976-02-05 |
JPS525506B2 (cs) | 1977-02-14 |
CA1039309A (en) | 1978-09-26 |
GB1445531A (en) | 1976-08-11 |
SU689613A3 (ru) | 1979-09-30 |
BG21011A3 (bg) | 1976-01-20 |
AU484223B2 (en) | 1977-06-14 |
ATA627574A (de) | 1977-01-15 |
RO76175A (ro) | 1981-05-30 |
BE818796A (fr) | 1974-12-02 |
ES429276A1 (es) | 1976-08-16 |
NL7410634A (nl) | 1975-02-18 |
JPS5062958A (cs) | 1975-05-29 |
CS189663B2 (en) | 1979-04-30 |
FR2240724B1 (cs) | 1978-07-28 |
AT338763B (de) | 1977-09-12 |
FI240074A7 (cs) | 1975-02-16 |
SE402583B (sv) | 1978-07-10 |
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