CS205109B2 - Způsob výroby esterů 3-substituovaných 2,2-dimethylcyklopropankarboxylovýcli kyselin - Google Patents

Způsob výroby esterů 3-substituovaných 2,2-dimethylcyklopropankarboxylovýcli kyselin Download PDF

Info

Publication number: CS205109B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; diene; difluoro; nmr; ethyl
Prior art date: 1977-01-24

Application number

CS749778A

Other languages

Czech (cs)

English (en)

Inventor

Roger K Huff

Original Assignee

Ici Ltd

Priority date (The priority date 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 date listed.)

1977-01-24

Filing date

1978-01-24

Publication date

1981-04-30

1978-01-24 Application filed by Ici Ltd filed Critical Ici Ltd

1981-04-30 Publication of CS205109B2 publication Critical patent/CS205109B2/cs

Links

239000002253 acid Substances 0.000 title description 2
150000007513 acids Chemical class 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims description 12
-1 3-substituted 2,2-dimethylcyclopropanecarboxylic acid esters Chemical class 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
150000001993 dienes Chemical class 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
MEDLDGIJDXFCBM-UHFFFAOYSA-N 2-diazobutanoic acid Chemical group CCC(=[N+]=[N-])C(O)=O MEDLDGIJDXFCBM-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 22
150000001875 compounds Chemical class 0.000 description 16
238000005481 NMR spectroscopy Methods 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
IFCIHMDXICWJFB-UHFFFAOYSA-N ClC(C(=C(C=C(C)C)C(F)F)Cl)(F)F Chemical compound ClC(C(=C(C=C(C)C)C(F)F)Cl)(F)F IFCIHMDXICWJFB-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
ALZFYKUYSWUHLE-UHFFFAOYSA-N 1,1,1-trifluoro-5-methyl-2-(trifluoromethyl)hex-4-en-2-ol Chemical compound CC(C)=CCC(O)(C(F)(F)F)C(F)(F)F ALZFYKUYSWUHLE-UHFFFAOYSA-N 0.000 description 3
IHHQSGSISUUYDB-UHFFFAOYSA-N 2-(difluoromethyl)-1,1,1-trifluoro-5-methylhex-4-en-2-ol Chemical compound CC(C)=CCC(O)(C(F)F)C(F)(F)F IHHQSGSISUUYDB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical compound OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
SRAKKNOEHFCVLC-UJURSFKZSA-N (1s,3s)-2,2-dimethyl-3-[3,3,3-trifluoro-2-(trifluoromethyl)prop-1-enyl]cyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(C(F)(F)F)C(F)(F)F)[C@@H]1C(O)=O SRAKKNOEHFCVLC-UJURSFKZSA-N 0.000 description 2
YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 2
FTMCNCGWNJMMQS-UHFFFAOYSA-M 3-methylbut-2-enyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=C(C)C)C1=CC=CC=C1 FTMCNCGWNJMMQS-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BSCUMHLWIBIQDT-UHFFFAOYSA-N CC(C)=CC=C(Cl)C(F)(F)C(F)F Chemical compound CC(C)=CC=C(Cl)C(F)(F)C(F)F BSCUMHLWIBIQDT-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
108010081348 HRT1 protein Hairy Proteins 0.000 description 2
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
REFMQCPSXDQGME-CRCLSJGQSA-N (1S,3S)-2,2-dimethyl-3-[3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]cyclopropane-1-carboxylic acid Chemical compound CC1([C@H]([C@@H]1C(=O)O)CC(C(F)(F)F)(C(F)(F)F)O)C REFMQCPSXDQGME-CRCLSJGQSA-N 0.000 description 1
WQAWXRFLNDAOON-UHFFFAOYSA-N 1,1,1,3,3-pentafluoropropan-2-one Chemical compound FC(F)C(=O)C(F)(F)F WQAWXRFLNDAOON-UHFFFAOYSA-N 0.000 description 1
IBHWVJDTSPHTJG-UHFFFAOYSA-N 1,1,1-trifluoro-5-methyl-2-(trifluoromethyl)hexa-2,4-diene Chemical compound CC(C)=CC=C(C(F)(F)F)C(F)(F)F IBHWVJDTSPHTJG-UHFFFAOYSA-N 0.000 description 1
QRKKTXWUDLJYCV-UHFFFAOYSA-N 1,3-dichloro-1,1,3,3-tetrafluoropropan-2-one Chemical compound FC(F)(Cl)C(=O)C(F)(F)Cl QRKKTXWUDLJYCV-UHFFFAOYSA-N 0.000 description 1
LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
VEQMUQZKBLIXLT-UHFFFAOYSA-N 2,3-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1C(C)C1C(O)=O VEQMUQZKBLIXLT-UHFFFAOYSA-N 0.000 description 1
GFMNEHCEZSAWPO-UHFFFAOYSA-N 2-(difluoromethyl)-1,1,1-trifluoro-5-methylhexa-2,4-diene Chemical class CC(C)=CC=C(C(F)F)C(F)(F)F GFMNEHCEZSAWPO-UHFFFAOYSA-N 0.000 description 1
WJUBBUUEZPOAGH-UHFFFAOYSA-N 2-(difluoromethyl)-1,1-difluoro-5-methylhexa-2,4-diene Chemical compound CC(C)=CC=C(C(F)F)C(F)F WJUBBUUEZPOAGH-UHFFFAOYSA-N 0.000 description 1
WLXTVRZYBKVORE-UHFFFAOYSA-N CC(=CCC(C(CF)(CF)CF)O)C Chemical compound CC(=CCC(C(CF)(CF)CF)O)C WLXTVRZYBKVORE-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012230 colorless oil Substances 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
150000001942 cyclopropanes Chemical class 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000000053 physical method Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CS749778A 1977-01-24 1978-01-24 Způsob výroby esterů 3-substituovaných 2,2-dimethylcyklopropankarboxylovýcli kyselin CS205109B2 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB276377		1977-01-24

Publications (1)

Publication Number	Publication Date
CS205109B2 true CS205109B2 (cs)	1981-04-30

Family

ID=9745446

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS749778A CS205109B2 (cs)	1977-01-24	1978-01-24	Způsob výroby esterů 3-substituovaných 2,2-dimethylcyklopropankarboxylovýcli kyselin

Country Status (7)

Country	Link
JP (2)	JPS61178950A (fr)
CS (1)	CS205109B2 (fr)
GE (1)	GEP19970942B (fr)
PL (2)	PL115315B1 (fr)
SU (1)	SU797540A3 (fr)
UA (1)	UA8255A1 (fr)
ZA (1)	ZA78420B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69835259T8 (de)	1997-01-22	2007-10-31	Advantest Corp.	System und verfahren zur optischen pulsübertragung

1978
- 1978-01-23 PL PL21703178A patent/PL115315B1/pl unknown
- 1978-01-23 SU SU782571453A patent/SU797540A3/ru active
- 1978-01-23 PL PL21703278A patent/PL114019B1/pl unknown
- 1978-01-23 UA UA2571453A patent/UA8255A1/uk unknown
- 1978-01-24 ZA ZA00780420A patent/ZA78420B/xx unknown
- 1978-01-24 CS CS749778A patent/CS205109B2/cs unknown
1986
- 1986-02-01 JP JP1921286A patent/JPS61178950A/ja active Granted
- 1986-02-01 JP JP1921186A patent/JPS61191640A/ja active Granted
1994
- 1994-05-16 GE GEAP19941936A patent/GEP19970942B/en unknown

Also Published As

Publication number	Publication date
JPS61191640A (ja)	1986-08-26
JPS61178950A (ja)	1986-08-11
JPS6236017B2 (fr)	1987-08-05
JPS6221776B2 (fr)	1987-05-14
UA8255A1 (uk)	1996-03-29
PL114019B1 (en)	1981-01-31
GEP19970942B (en)	1997-04-18
ZA78420B (en)	1979-09-26
SU797540A3 (ru)	1981-01-15
PL115315B1 (en)	1981-03-31

Publication	Publication Date	Title
SE445735B (sv)	1986-07-14	Kemisk forening till anvendning som mellanprodukt vid framstellning av cyklopropanderivat med insekticida egenskaper jemte sett for dess framstellning
EP0006205B1 (fr)	1982-09-22	Procédé pour la préparation de dérivés d'acides chlorostyrène cyclopropane carboxyliques
DK174496B1 (da)	2003-04-22	Fremgangsmåde til fremstilling af 5-(2,5-dimethylphenoxy)-2,2-dimethylpentansyre
EP0294774B1 (fr)	1993-01-13	Procédé de préparation d'esters de l'acide gamma-halogène téglinique et leur transformation en alkylesters de l'acide 0,0-dialkyl-gamma-phosphono-téglinique
EP0221635B1 (fr)	1990-03-14	Alcools fluorés et leurs esters insecticides
US4229353A (en)	1980-10-21	(2,2-Disubstituted vinyl)γ-butyrolactones
US4442301A (en)	1984-04-10	Process for stereoselectively synthesizing cyclopropane carboxylates
US4302612A (en)	1981-11-24	Synthesis of perfluorodialdehydes
US4474980A (en)	1984-10-02	Process for the preparation of intermediates for pyrethroids
US4450296A (en)	1984-05-22	Process for the production of arylalkanone and intermediate
EP0937730B1 (fr)	2000-08-30	Procédé de préparation d'amides d'acides carboxyliques silylés
CH644093A5 (de)	1984-07-13	Verfahren zur herstellung von 2,2-dihalogenvinyl-substituierten cyclopropancarbonsaeure-estern.
EP0290903B1 (fr)	1991-09-11	Bêta-fluoracyl-bêta-halogénovinyl alkyl éthers
EP0010856B1 (fr)	1982-10-27	Hydrocarbures halogénés et procédé pour leur préparation
EP0031915B1 (fr)	1983-05-25	Procédé pour la préparation d'halogénoalcènes
CH641135A5 (en)	1984-02-15	Alkadienes and alkenols
PL115315B1 (en)	1981-03-31	Method of halogen compounds manufacture
EP0647640B1 (fr)	1999-03-24	Procédé pour la préparation de dérivés de pilocarpine
US4092482A (en)	1978-05-30	Process for preparing 6,6,6-trihalo-3,3-dimethyl-4-hexenoates
JPH0145460B2 (fr)	1989-10-03
HU191904B (en)	1987-04-28	Process for preparing derivatives of cyclopropancarboxylic acid
GB1601345A (en)	1981-10-28	Alkenols
EP0019719A1 (fr)	1980-12-10	Procédé de préparation d'alcènes, nouveaux intermédiaires pour leur préparation et procédé de les préparer
GB1601346A (en)	1981-10-28	Alkadienes
JP3541421B2 (ja)	2004-07-14	含アレン−α−置換シクロペンテノン誘導体及びその製造方法