UA74994C2 - A method for producing 3-trifluoromethylphenyl-4-cyanobenzyl ketone - Google Patents
A method for producing 3-trifluoromethylphenyl-4-cyanobenzyl ketone Download PDFInfo
- Publication number
- UA74994C2 UA74994C2 UA20041109647A UA20041109647A UA74994C2 UA 74994 C2 UA74994 C2 UA 74994C2 UA 20041109647 A UA20041109647 A UA 20041109647A UA 20041109647 A UA20041109647 A UA 20041109647A UA 74994 C2 UA74994 C2 UA 74994C2
- Authority
- UA
- Ukraine
- Prior art keywords
- aprotic polar
- base
- trifluoromethylphenyl
- reaction
- fact
- Prior art date
Links
- CNVRUUHGVUPTCK-UHFFFAOYSA-N 4-[3-(4-cyanophenyl)-2-oxo-1,3-bis[3-(trifluoromethyl)phenyl]propyl]benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C(C(=O)C(C=2C=CC(=CC=2)C#N)C=2C=C(C=CC=2)C(F)(F)F)C=2C=CC(=CC=2)C#N)=C1 CNVRUUHGVUPTCK-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 239000002798 polar solvent Substances 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000011591 potassium Substances 0.000 claims abstract description 8
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 8
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- FQXQBFUUVCDIRK-UHFFFAOYSA-N 3-trifluoromethylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C(F)(F)F)=C1 FQXQBFUUVCDIRK-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000003993 interaction Effects 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000002585 base Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000012454 non-polar solvent Substances 0.000 description 5
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
- 239000002253 acid Substances 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- -1 diethylene glycol dialkyl ethers Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- FBRJYBGLCHWYOE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(F)(F)F FBRJYBGLCHWYOE-UHFFFAOYSA-N 0.000 description 1
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 1
- USFLKKYPNZZZDX-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C(C1=CC=C(C=C1)C#N)C(=O)C(C1=CC=C(C=C1)C#N)C1=CC(=CC=C1)Cl Chemical compound ClC=1C=C(C=CC=1)C(C1=CC=C(C=C1)C#N)C(=O)C(C1=CC=C(C=C1)C#N)C1=CC(=CC=C1)Cl USFLKKYPNZZZDX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229940052296 esters of benzoic acid for local anesthesia Drugs 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10218764 | 2002-04-26 | ||
| PCT/EP2003/004327 WO2003091203A1 (de) | 2002-04-26 | 2003-04-25 | Verfahren zur herstellung von 3-trifluormethylphenyl-4-cyanobenzylketon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA74994C2 true UA74994C2 (en) | 2006-02-15 |
Family
ID=29264861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20041109647A UA74994C2 (en) | 2002-04-26 | 2003-04-25 | A method for producing 3-trifluoromethylphenyl-4-cyanobenzyl ketone |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6992206B2 (ko) |
| EP (1) | EP1501788B1 (ko) |
| JP (1) | JP4065241B2 (ko) |
| KR (1) | KR100949207B1 (ko) |
| CN (1) | CN1268606C (ko) |
| AR (1) | AR039457A1 (ko) |
| AT (1) | ATE464285T1 (ko) |
| AU (1) | AU2003224128B2 (ko) |
| BR (1) | BR0309193B1 (ko) |
| CA (1) | CA2482414C (ko) |
| DE (1) | DE50312617D1 (ko) |
| DK (1) | DK1501788T3 (ko) |
| EA (1) | EA006976B1 (ko) |
| ES (1) | ES2343175T3 (ko) |
| IL (2) | IL164297A0 (ko) |
| MX (1) | MXPA04009786A (ko) |
| PL (1) | PL205212B1 (ko) |
| SI (1) | SI1501788T1 (ko) |
| UA (1) | UA74994C2 (ko) |
| WO (1) | WO2003091203A1 (ko) |
| ZA (1) | ZA200409518B (ko) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3002791B2 (ja) * | 1990-12-29 | 2000-01-24 | 日本農薬株式会社 | ベンジルフェニルケトン誘導体 |
-
2003
- 2003-04-25 CN CNB038093812A patent/CN1268606C/zh not_active Expired - Lifetime
- 2003-04-25 PL PL371769A patent/PL205212B1/pl not_active IP Right Cessation
- 2003-04-25 CA CA2482414A patent/CA2482414C/en not_active Expired - Fee Related
- 2003-04-25 KR KR1020047017195A patent/KR100949207B1/ko not_active IP Right Cessation
- 2003-04-25 ES ES03720529T patent/ES2343175T3/es not_active Expired - Lifetime
- 2003-04-25 SI SI200331818T patent/SI1501788T1/sl unknown
- 2003-04-25 UA UA20041109647A patent/UA74994C2/uk unknown
- 2003-04-25 DE DE50312617T patent/DE50312617D1/de not_active Expired - Lifetime
- 2003-04-25 MX MXPA04009786A patent/MXPA04009786A/es active IP Right Grant
- 2003-04-25 IL IL16429703A patent/IL164297A0/xx active IP Right Grant
- 2003-04-25 AU AU2003224128A patent/AU2003224128B2/en not_active Expired
- 2003-04-25 WO PCT/EP2003/004327 patent/WO2003091203A1/de active Application Filing
- 2003-04-25 EA EA200401380A patent/EA006976B1/ru not_active IP Right Cessation
- 2003-04-25 AR ARP030101446A patent/AR039457A1/es active IP Right Grant
- 2003-04-25 JP JP2003587768A patent/JP4065241B2/ja not_active Expired - Lifetime
- 2003-04-25 BR BRPI0309193-7A patent/BR0309193B1/pt active IP Right Grant
- 2003-04-25 DK DK03720529.1T patent/DK1501788T3/da active
- 2003-04-25 AT AT03720529T patent/ATE464285T1/de active
- 2003-04-25 US US10/512,487 patent/US6992206B2/en not_active Expired - Lifetime
- 2003-04-25 EP EP03720529A patent/EP1501788B1/de not_active Expired - Lifetime
-
2004
- 2004-09-27 IL IL164297A patent/IL164297A/en unknown
- 2004-11-25 ZA ZA200409518A patent/ZA200409518B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2482414A1 (en) | 2003-11-06 |
| ZA200409518B (en) | 2006-06-28 |
| DK1501788T3 (da) | 2010-07-26 |
| BR0309193B1 (pt) | 2013-05-28 |
| BR0309193A (pt) | 2005-02-09 |
| DE50312617D1 (de) | 2010-05-27 |
| SI1501788T1 (sl) | 2010-07-30 |
| CN1649832A (zh) | 2005-08-03 |
| JP2005523919A (ja) | 2005-08-11 |
| WO2003091203A1 (de) | 2003-11-06 |
| JP4065241B2 (ja) | 2008-03-19 |
| PL205212B1 (pl) | 2010-03-31 |
| CN1268606C (zh) | 2006-08-09 |
| ES2343175T3 (es) | 2010-07-26 |
| IL164297A0 (en) | 2005-12-18 |
| KR20040104631A (ko) | 2004-12-10 |
| IL164297A (en) | 2009-02-11 |
| AR039457A1 (es) | 2005-02-23 |
| AU2003224128A1 (en) | 2003-11-10 |
| US6992206B2 (en) | 2006-01-31 |
| EA006976B1 (ru) | 2006-06-30 |
| US20050171373A1 (en) | 2005-08-04 |
| AU2003224128B2 (en) | 2009-03-19 |
| CA2482414C (en) | 2010-11-16 |
| EP1501788A1 (de) | 2005-02-02 |
| PL371769A1 (en) | 2005-06-27 |
| EA200401380A1 (ru) | 2005-04-28 |
| EP1501788B1 (de) | 2010-04-14 |
| KR100949207B1 (ko) | 2010-03-24 |
| MXPA04009786A (es) | 2004-12-13 |
| ATE464285T1 (de) | 2010-04-15 |
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