JPS62905B2 - - Google Patents
Info
- Publication number
- JPS62905B2 JPS62905B2 JP53106541A JP10654178A JPS62905B2 JP S62905 B2 JPS62905 B2 JP S62905B2 JP 53106541 A JP53106541 A JP 53106541A JP 10654178 A JP10654178 A JP 10654178A JP S62905 B2 JPS62905 B2 JP S62905B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- compound
- reaction
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 nitrile compound Chemical class 0.000 claims description 70
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 76
- 238000006243 chemical reaction Methods 0.000 description 59
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 26
- 238000000034 method Methods 0.000 description 25
- 239000002904 solvent Substances 0.000 description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical class CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- 150000001340 alkali metals Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000011437 continuous method Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000006502 nitrobenzyl group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 2
- ZICDZTXDTPZBKH-UHFFFAOYSA-N 2-(4-methylphenyl)-1-phenylethanamine Chemical compound C1=CC(C)=CC=C1CC(N)C1=CC=CC=C1 ZICDZTXDTPZBKH-UHFFFAOYSA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 1
- DTGGNTMERRTPLR-UHFFFAOYSA-N 1,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=CC=C1 DTGGNTMERRTPLR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WQLQKKZHEUQVBU-UHFFFAOYSA-N 1-(1-chloroethyl)-4-methylbenzene Chemical compound CC(Cl)C1=CC=C(C)C=C1 WQLQKKZHEUQVBU-UHFFFAOYSA-N 0.000 description 1
- UGQMEEXNQQOBHB-UHFFFAOYSA-N 1-(2,4-dibromophenyl)-2-(2,5-dimethylphenyl)ethanamine Chemical compound CC1=CC=C(C)C(CC(N)C=2C(=CC(Br)=CC=2)Br)=C1 UGQMEEXNQQOBHB-UHFFFAOYSA-N 0.000 description 1
- IKQUIEUIEOSARW-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-phenylethanamine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(N)CC1=CC=CC=C1 IKQUIEUIEOSARW-UHFFFAOYSA-N 0.000 description 1
- TWSNTNTURYXFGS-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-3-phenylpropan-1-amine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(N)CCC1=CC=CC=C1 TWSNTNTURYXFGS-UHFFFAOYSA-N 0.000 description 1
- KCGUKZPENYAQMF-UHFFFAOYSA-N 1-(2,5-dibromophenyl)-2-(3,4-dimethylphenyl)ethanamine Chemical compound C1=C(C)C(C)=CC=C1CC(N)C1=CC(Br)=CC=C1Br KCGUKZPENYAQMF-UHFFFAOYSA-N 0.000 description 1
- XWDNINXHEUCGDN-UHFFFAOYSA-N 1-(3,4-dibromophenyl)-2-(2,4-dichlorophenyl)ethanamine Chemical compound C=1C=C(Br)C(Br)=CC=1C(N)CC1=CC=C(Cl)C=C1Cl XWDNINXHEUCGDN-UHFFFAOYSA-N 0.000 description 1
- NUEZSCSONNUBQX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-phenylethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(N)CC1=CC=CC=C1 NUEZSCSONNUBQX-UHFFFAOYSA-N 0.000 description 1
- FYCLZRHMPRTQBG-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-2-(2,4-dimethylphenyl)ethanamine Chemical compound CC1=CC(C)=CC=C1CC(N)C1=CC=C(F)C(F)=C1 FYCLZRHMPRTQBG-UHFFFAOYSA-N 0.000 description 1
- WAKRXOCPJKLWAS-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-2-phenylethanamine Chemical compound C1=C(OC)C(OC)=CC=C1C(N)CC1=CC=CC=C1 WAKRXOCPJKLWAS-UHFFFAOYSA-N 0.000 description 1
- NIHHNNTWIYOYRE-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-2-phenylethanamine Chemical compound C1=C(C)C(C)=CC=C1C(N)CC1=CC=CC=C1 NIHHNNTWIYOYRE-UHFFFAOYSA-N 0.000 description 1
- VVJATHWMCGHNDW-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-2-phenylethanamine Chemical compound C=1C(Cl)=CC(Cl)=CC=1C(N)CC1=CC=CC=C1 VVJATHWMCGHNDW-UHFFFAOYSA-N 0.000 description 1
- XGASTRVQNVVYIZ-UHFFFAOYSA-N 1-(chloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(CCl)=C1 XGASTRVQNVVYIZ-UHFFFAOYSA-N 0.000 description 1
- XBDXMDVEZLOGMC-UHFFFAOYSA-N 1-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCl)=C1 XBDXMDVEZLOGMC-UHFFFAOYSA-N 0.000 description 1
- VGISFWWEOGVMED-UHFFFAOYSA-N 1-(chloromethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CCl)=C1 VGISFWWEOGVMED-UHFFFAOYSA-N 0.000 description 1
- LZBOHNCMCCSTJX-UHFFFAOYSA-N 1-(chloromethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CCl)=C1 LZBOHNCMCCSTJX-UHFFFAOYSA-N 0.000 description 1
- QUYVTGFWFHQVRO-UHFFFAOYSA-N 1-(chloromethyl)-3-phenoxybenzene Chemical compound ClCC1=CC=CC(OC=2C=CC=CC=2)=C1 QUYVTGFWFHQVRO-UHFFFAOYSA-N 0.000 description 1
- RVQOLTBRWHPYTM-UHFFFAOYSA-N 1-(chloromethyl)-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(CCl)C=C1 RVQOLTBRWHPYTM-UHFFFAOYSA-N 0.000 description 1
- SLRZFIXJBDNRAG-UHFFFAOYSA-N 1-(chloromethyl)-4-(trichloromethyl)benzene Chemical compound ClCC1=CC=C(C(Cl)(Cl)Cl)C=C1 SLRZFIXJBDNRAG-UHFFFAOYSA-N 0.000 description 1
- MCHDHQVROPEJJT-UHFFFAOYSA-N 1-(chloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CCl)C=C1 MCHDHQVROPEJJT-UHFFFAOYSA-N 0.000 description 1
- DCLMJYZEOSDVCL-UHFFFAOYSA-N 1-(chloromethyl)-4-ethoxybenzene Chemical compound CCOC1=CC=C(CCl)C=C1 DCLMJYZEOSDVCL-UHFFFAOYSA-N 0.000 description 1
- DUBCVXSYZVTCOC-UHFFFAOYSA-N 1-(chloromethyl)-4-ethylbenzene Chemical compound CCC1=CC=C(CCl)C=C1 DUBCVXSYZVTCOC-UHFFFAOYSA-N 0.000 description 1
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 description 1
- LXPRVXKHIXWBJZ-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(CCl)C=C1 LXPRVXKHIXWBJZ-UHFFFAOYSA-N 0.000 description 1
- IATNZRYVIRYKDJ-UHFFFAOYSA-N 1-(chloromethyl)-4-phenoxybenzene Chemical compound C1=CC(CCl)=CC=C1OC1=CC=CC=C1 IATNZRYVIRYKDJ-UHFFFAOYSA-N 0.000 description 1
- RLFHPRWHJYDGSD-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylsulfanylbenzene Chemical compound C1=CC(CCl)=CC=C1SC1=CC=CC=C1 RLFHPRWHJYDGSD-UHFFFAOYSA-N 0.000 description 1
- ZMSZCUFHPKUFSI-UHFFFAOYSA-N 1-(chloromethyl)-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(CCl)C=C1 ZMSZCUFHPKUFSI-UHFFFAOYSA-N 0.000 description 1
- CYAKWEQUWJAHLW-UHFFFAOYSA-N 1-(chloromethyl)-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(CCl)C=C1 CYAKWEQUWJAHLW-UHFFFAOYSA-N 0.000 description 1
- OCGNQJCQAQWYOI-UHFFFAOYSA-N 1-(chloromethyl)-4-propylbenzene Chemical compound CCCC1=CC=C(CCl)C=C1 OCGNQJCQAQWYOI-UHFFFAOYSA-N 0.000 description 1
- KFQWWEALJZQIMQ-UHFFFAOYSA-N 1-[chloro(methoxy)methyl]-4-methylbenzene Chemical compound COC(Cl)C1=CC=C(C)C=C1 KFQWWEALJZQIMQ-UHFFFAOYSA-N 0.000 description 1
- GZPMYEQKMRYMDI-UHFFFAOYSA-N 1-[chloro(methoxy)methyl]-4-methylsulfonylbenzene Chemical compound COC(Cl)C1=CC=C(S(C)(=O)=O)C=C1 GZPMYEQKMRYMDI-UHFFFAOYSA-N 0.000 description 1
- UDKGXKYEWBGQCG-UHFFFAOYSA-N 1-bromo-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Br)=C1 UDKGXKYEWBGQCG-UHFFFAOYSA-N 0.000 description 1
- BSIIGUGKOPPTPZ-UHFFFAOYSA-N 1-bromo-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Br)C=C1 BSIIGUGKOPPTPZ-UHFFFAOYSA-N 0.000 description 1
- ZFZDHCZLDOAJCA-UHFFFAOYSA-N 1-butyl-4-(chloromethyl)benzene Chemical compound CCCCC1=CC=C(CCl)C=C1 ZFZDHCZLDOAJCA-UHFFFAOYSA-N 0.000 description 1
- DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- 125000006184 2,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- KUDQZZYAXCXZBG-UHFFFAOYSA-N 2-(2,4-dibromophenyl)-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=C(Br)C=C1Br KUDQZZYAXCXZBG-UHFFFAOYSA-N 0.000 description 1
- LSVPOOSMMAKAFL-UHFFFAOYSA-N 2-(2,5-dibromophenyl)-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC(Br)=CC=C1Br LSVPOOSMMAKAFL-UHFFFAOYSA-N 0.000 description 1
- OVBJDQAWTPHAST-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC(F)=CC=C1F OVBJDQAWTPHAST-UHFFFAOYSA-N 0.000 description 1
- UCEQOIKTSMMZMI-UHFFFAOYSA-N 2-(3,4-dibromophenyl)-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=C(Br)C(Br)=C1 UCEQOIKTSMMZMI-UHFFFAOYSA-N 0.000 description 1
- QALDPJNZWNCOQC-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-1-(2,4-dimethylphenyl)ethanamine Chemical compound CC1=CC(C)=CC=C1C(N)CC1=CC=C(Cl)C(Cl)=C1 QALDPJNZWNCOQC-UHFFFAOYSA-N 0.000 description 1
- TUEPTNGVJHHULV-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=C(F)C(F)=C1 TUEPTNGVJHHULV-UHFFFAOYSA-N 0.000 description 1
- ASFOYLALGQHYJG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-(2,5-dimethylphenyl)ethanamine Chemical compound C1=C(OC)C(OC)=CC=C1CC(N)C1=CC(C)=CC=C1C ASFOYLALGQHYJG-UHFFFAOYSA-N 0.000 description 1
- JFQGNGSPNHPEIO-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-3-phenylpropanamide Chemical compound C=1C=CC(O)=CC=1C(C(=O)N)CC1=CC=CC=C1 JFQGNGSPNHPEIO-UHFFFAOYSA-N 0.000 description 1
- FLYWEWFLPROFAK-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-3-phenylpropanenitrile Chemical compound OC1=CC=CC(C(CC=2C=CC=CC=2)C#N)=C1 FLYWEWFLPROFAK-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- CJDOBRDRLARBDC-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-(2,4-dimethylphenyl)propanamide Chemical compound CC1=CC(C)=CC=C1C(C(N)=O)CC1=CC=C(Cl)C(Cl)=C1 CJDOBRDRLARBDC-UHFFFAOYSA-N 0.000 description 1
- WOPUERCEBTWCSC-UHFFFAOYSA-N 3-(4-methylphenyl)-2-phenylpropanamide Chemical compound C1=CC(C)=CC=C1CC(C(N)=O)C1=CC=CC=C1 WOPUERCEBTWCSC-UHFFFAOYSA-N 0.000 description 1
- DSEPEFQVRBOMGM-UHFFFAOYSA-N 3-(4-methylphenyl)-2-phenylpropanenitrile Chemical compound C1=CC(C)=CC=C1CC(C#N)C1=CC=CC=C1 DSEPEFQVRBOMGM-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 1
- XZBXAYCCBFTQHH-UHFFFAOYSA-N 3-chloropropylbenzene Chemical compound ClCCCC1=CC=CC=C1 XZBXAYCCBFTQHH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CITRPMHCVVMQDU-UHFFFAOYSA-N 4-(chloromethyl)-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(CCl)C=C1 CITRPMHCVVMQDU-UHFFFAOYSA-N 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- IYDQKYUTOJKBNX-UHFFFAOYSA-L CC[N+](CC)(CC)CC1=CC=CC=C1.CC[N+](CC)(CC)CC1=CC=CC=C1.[OH-].[Cl-] Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1.CC[N+](CC)(CC)CC1=CC=CC=C1.[OH-].[Cl-] IYDQKYUTOJKBNX-UHFFFAOYSA-L 0.000 description 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AXETWCLURMFYDG-UHFFFAOYSA-N ClCC(C=CC(Cl)=C1)=C1Cl.Br Chemical compound ClCC(C=CC(Cl)=C1)=C1Cl.Br AXETWCLURMFYDG-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000006105 Hofmann reaction Methods 0.000 description 1
- 238000007192 Meerwein reaction reaction Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 229910000756 V alloy Inorganic materials 0.000 description 1
- OWISXYQFTOYGRO-UHFFFAOYSA-N Xylylic acid nitrile Natural products CC1=CC=C(C#N)C=C1C OWISXYQFTOYGRO-UHFFFAOYSA-N 0.000 description 1
- OGALXJIOJZXBBP-UHFFFAOYSA-N [4-(chloromethyl)phenyl]methanol Chemical compound OCC1=CC=C(CCl)C=C1 OGALXJIOJZXBBP-UHFFFAOYSA-N 0.000 description 1
- XLLKUFRSCJFAHF-UHFFFAOYSA-N [Cu].[Mg].[Cr] Chemical compound [Cu].[Mg].[Cr] XLLKUFRSCJFAHF-UHFFFAOYSA-N 0.000 description 1
- COVIHMADWYEBTP-UHFFFAOYSA-N [chloro(methylsulfanyl)methyl]benzene Chemical compound CSC(Cl)C1=CC=CC=C1 COVIHMADWYEBTP-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- XVDWMONETMNKBK-UHFFFAOYSA-N calcium;dihypobromite Chemical compound [Ca+2].Br[O-].Br[O-] XVDWMONETMNKBK-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- LTYZGLKKXZXSEC-UHFFFAOYSA-N copper dihydride Chemical compound [CuH2] LTYZGLKKXZXSEC-UHFFFAOYSA-N 0.000 description 1
- 229910000050 copper hydride Inorganic materials 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- RPYFZMPJOHSVLD-UHFFFAOYSA-N copper vanadium Chemical compound [V][V][Cu] RPYFZMPJOHSVLD-UHFFFAOYSA-N 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 230000000382 dechlorinating effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- JEUXZUSUYIHGNL-UHFFFAOYSA-N n,n-diethylethanamine;hydrate Chemical compound O.CCN(CC)CC JEUXZUSUYIHGNL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
- ORQYPOUSZINNCB-UHFFFAOYSA-N potassium;hypobromite Chemical compound [K+].Br[O-] ORQYPOUSZINNCB-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- ZOHPSQXYSYQRBR-UHFFFAOYSA-L tetraethylazanium chloride hydroxide Chemical compound [OH-].[Cl-].CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC ZOHPSQXYSYQRBR-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10654178A JPS5533442A (en) | 1978-08-30 | 1978-08-30 | Preparation of amine derivative |
| EP81200767A EP0040896B1 (de) | 1978-08-22 | 1979-08-20 | Synthese von Amiden |
| DE8181200767T DE2966944D1 (en) | 1978-08-22 | 1979-08-20 | Synthesis of amides |
| DE7979301696T DE2965916D1 (en) | 1978-08-22 | 1979-08-20 | Synthesis of amines |
| EP79301696A EP0008532B1 (de) | 1978-08-22 | 1979-08-20 | Synthese von Aminen |
| US06/090,479 US4536599A (en) | 1978-08-22 | 1979-11-01 | Synthesis of amine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10654178A JPS5533442A (en) | 1978-08-30 | 1978-08-30 | Preparation of amine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5533442A JPS5533442A (en) | 1980-03-08 |
| JPS62905B2 true JPS62905B2 (de) | 1987-01-10 |
Family
ID=14436225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10654178A Granted JPS5533442A (en) | 1978-08-22 | 1978-08-30 | Preparation of amine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5533442A (de) |
-
1978
- 1978-08-30 JP JP10654178A patent/JPS5533442A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5533442A (en) | 1980-03-08 |
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