TWI229065B - Chemical process for the preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol - Google Patents
Chemical process for the preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol Download PDFInfo
- Publication number
- TWI229065B TWI229065B TW090126037A TW90126037A TWI229065B TW I229065 B TWI229065 B TW I229065B TW 090126037 A TW090126037 A TW 090126037A TW 90126037 A TW90126037 A TW 90126037A TW I229065 B TWI229065 B TW I229065B
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- item
- patent application
- scope
- fluorenyl
- Prior art date
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- PJCSTULKVNHEGW-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methanol Chemical compound CC1=C(F)C(F)=C(CO)C(F)=C1F PJCSTULKVNHEGW-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000001311 chemical methods and process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 17
- AYCZMWCDBIZDAD-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methanamine Chemical compound CC1=C(F)C(F)=C(CN)C(F)=C1F AYCZMWCDBIZDAD-UHFFFAOYSA-N 0.000 claims abstract description 5
- NUSQQHOHSBCDQX-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-methylbenzonitrile Chemical compound CC1=C(F)C(F)=C(C#N)C(F)=C1F NUSQQHOHSBCDQX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- -1 chloromethyl Chemical group 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- KSGLXMCBJYLAFD-UHFFFAOYSA-N 1-(2,3,5,6-tetrafluorophenyl)ethanol Chemical compound CC(O)C1=C(F)C(F)=CC(F)=C1F KSGLXMCBJYLAFD-UHFFFAOYSA-N 0.000 claims 1
- CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 229960000583 acetic acid Drugs 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YRDCJXZAEUBTMS-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methyl acetate Chemical compound CC(=O)OCC1=C(F)C(F)=C(C)C(F)=C1F YRDCJXZAEUBTMS-UHFFFAOYSA-N 0.000 description 1
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 1
- SOZFIIXUNAKEJP-UHFFFAOYSA-N 1,2,3,4-tetrafluorobenzene Chemical compound FC1=CC=C(F)C(F)=C1F SOZFIIXUNAKEJP-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000238558 Eucarida Species 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000005939 Tefluthrin Substances 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- AFMVESZOYKHDBJ-UHFFFAOYSA-N fluoren-9-ol Chemical class C1=CC=C2C(O)C3=CC=CC=C3C2=C1 AFMVESZOYKHDBJ-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229940040145 liniment Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KATMMOGJSFLTOP-UHFFFAOYSA-N tetradecan-6-ol Chemical compound CCCCCCCCC(O)CCCCC KATMMOGJSFLTOP-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- 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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0026348.3A GB0026348D0 (en) | 2000-10-27 | 2000-10-27 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI229065B true TWI229065B (en) | 2005-03-11 |
Family
ID=9902107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090126037A TWI229065B (en) | 2000-10-27 | 2001-10-22 | Chemical process for the preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6894195B2 (https=) |
| EP (1) | EP1332125B1 (https=) |
| JP (1) | JP3984913B2 (https=) |
| KR (1) | KR100788927B1 (https=) |
| CN (1) | CN1213992C (https=) |
| AT (1) | ATE277885T1 (https=) |
| AU (1) | AU2002210695A1 (https=) |
| BR (1) | BR0114931B1 (https=) |
| DE (1) | DE60106073T2 (https=) |
| GB (1) | GB0026348D0 (https=) |
| HU (1) | HU228240B1 (https=) |
| IL (2) | IL155200A0 (https=) |
| TW (1) | TWI229065B (https=) |
| WO (1) | WO2002034707A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101193843B (zh) | 2005-06-22 | 2011-05-04 | 昭和电工株式会社 | 环卤化的甲基苯甲醇的制备方法 |
| EP2123624B1 (en) * | 2007-02-16 | 2013-04-17 | Sumitomo Chemical Company, Limited | Method for producing 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol |
| CN102617279B (zh) * | 2012-03-31 | 2014-06-11 | 浙江工业大学 | 一种由胺类化合物制备醇类化合物的方法 |
| AU2017203635B2 (en) | 2017-05-30 | 2022-02-03 | Rotam Agrochem International Company Limited | A novel crystalline form of tefluthrin, a process for its preparation and use of the same |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3406024A (en) * | 1965-08-27 | 1968-10-15 | Velsicol Chemical Corp | Method for the control of weeds |
| DE3065914D1 (en) | 1979-12-21 | 1984-01-19 | Ici Plc | Substituted benzyl esters of cyclopropane carboxylic acids and their preparation, compositions containing them and methods of combating insect pests therewith, and substituted benzyl alcohols |
| GB2123823B (en) * | 1982-07-21 | 1985-12-04 | Ici Plc | 4-methyl-2 3 5 6-tetrafluorobenzaldiacetate and a process for its preparation |
| GB2123824B (en) * | 1982-07-21 | 1986-07-30 | Ici Plc | 4-methyl-2 3 5 6-tetrafluorobenzyl acetate and a process for its preparation |
| GB2127013B (en) * | 1982-09-17 | 1985-12-11 | Ici Plc | Tetrafluoroterephthalyl alcohol esters thereof and a process for their preparation |
| DE3714602A1 (de) * | 1987-05-01 | 1988-11-10 | Bayer Ag | Verfahren zur herstellung von 2,3,5,6-tetrafluor-benzyl-alkoholen |
| DE19780906B4 (de) * | 1996-08-29 | 2007-04-19 | Showa Denko K.K. | Verfahren zur Herstellung von Benzonitril und Benzylalkohol |
| JP2000086583A (ja) * | 1998-09-17 | 2000-03-28 | Asahi Glass Co Ltd | 含フッ素ベンジル誘導体の製造方法 |
| JP2001294560A (ja) * | 2000-04-13 | 2001-10-23 | Central Glass Co Ltd | トリフルオロメチルベンジルアミン類の製造方法 |
| JP2003089679A (ja) * | 2001-09-17 | 2003-03-28 | Nippon Shokubai Co Ltd | 含フッ素アミン化合物 |
| JP2003089664A (ja) * | 2001-09-17 | 2003-03-28 | Nippon Shokubai Co Ltd | 含フッ素パラシクロファンの製法 |
-
2000
- 2000-10-27 GB GBGB0026348.3A patent/GB0026348D0/en not_active Ceased
-
2001
- 2001-10-18 EP EP01978595A patent/EP1332125B1/en not_active Expired - Lifetime
- 2001-10-18 AT AT01978595T patent/ATE277885T1/de not_active IP Right Cessation
- 2001-10-18 JP JP2002537701A patent/JP3984913B2/ja not_active Expired - Fee Related
- 2001-10-18 CN CNB018180205A patent/CN1213992C/zh not_active Expired - Fee Related
- 2001-10-18 AU AU2002210695A patent/AU2002210695A1/en not_active Abandoned
- 2001-10-18 KR KR1020037005664A patent/KR100788927B1/ko not_active Expired - Fee Related
- 2001-10-18 IL IL15520001A patent/IL155200A0/xx unknown
- 2001-10-18 WO PCT/GB2001/004692 patent/WO2002034707A1/en not_active Ceased
- 2001-10-18 HU HU0301158A patent/HU228240B1/hu not_active IP Right Cessation
- 2001-10-18 BR BRPI0114931-8A patent/BR0114931B1/pt not_active IP Right Cessation
- 2001-10-18 DE DE60106073T patent/DE60106073T2/de not_active Expired - Lifetime
- 2001-10-18 US US10/415,262 patent/US6894195B2/en not_active Expired - Fee Related
- 2001-10-22 TW TW090126037A patent/TWI229065B/zh not_active IP Right Cessation
-
2003
- 2003-04-02 IL IL155200A patent/IL155200A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB0026348D0 (en) | 2000-12-13 |
| BR0114931A (pt) | 2004-01-06 |
| JP2004512320A (ja) | 2004-04-22 |
| CN1494525A (zh) | 2004-05-05 |
| WO2002034707A1 (en) | 2002-05-02 |
| BR0114931B1 (pt) | 2012-03-20 |
| CN1213992C (zh) | 2005-08-10 |
| IL155200A0 (en) | 2003-11-23 |
| ATE277885T1 (de) | 2004-10-15 |
| EP1332125A1 (en) | 2003-08-06 |
| HUP0301158A2 (en) | 2007-03-28 |
| US20040063993A1 (en) | 2004-04-01 |
| KR20030044032A (ko) | 2003-06-02 |
| IL155200A (en) | 2010-04-15 |
| HU228240B1 (hu) | 2013-02-28 |
| HUP0301158A3 (en) | 2007-06-28 |
| EP1332125B1 (en) | 2004-09-29 |
| JP3984913B2 (ja) | 2007-10-03 |
| US6894195B2 (en) | 2005-05-17 |
| DE60106073T2 (de) | 2006-03-09 |
| AU2002210695A1 (en) | 2002-05-06 |
| DE60106073D1 (de) | 2004-11-04 |
| KR100788927B1 (ko) | 2007-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |