DD144912A5 - Verfahren fuer die herstellung von zwischenverbindungen fuer die darstellung von cyclopropancarboxylatester - Google Patents

Verfahren fuer die herstellung von zwischenverbindungen fuer die darstellung von cyclopropancarboxylatester Download PDF

Info

Publication number: DD144912A5
Authority: DD; German Democratic Republic
Prior art keywords: tri; phosphine; item; compounds; general formula
Prior art date: 1978-07-19

Application number

DD79214408A

Other languages

German (de)

English (en)

Inventor

Berkel Johannes Van

Hendrik C Kelderman

Pieter A Verbrugge

Petrus A Kramer

Johannes L M Syrier

Original Assignee

Shell Int Research

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.)

1978-07-19

Filing date

1979-07-17

Publication date

1980-11-12

1979-07-17 Application filed by Shell Int Research filed Critical Shell Int Research

1980-11-12 Publication of DD144912A5 publication Critical patent/DD144912A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims abstract description 12
150000001875 compounds Chemical class 0.000 claims abstract description 37
125000005843 halogen group Chemical group 0.000 claims abstract description 4
241000251730 Chondrichthyes Species 0.000 claims abstract description 3
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 16
-1 phosphine tri (diethylamino) phosphine Chemical compound 0.000 claims description 14
125000004663 dialkyl amino group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 8
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 8
BQOFWKZOCNGFEC-UHFFFAOYSA-N Delta3-Carene Natural products C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims description 6
150000001335 aliphatic alkanes Chemical group 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 6
BQOFWKZOCNGFEC-BDAKNGLRSA-N (+)-Delta3-carene Chemical compound C1C(C)=CC[C@H]2C(C)(C)[C@@H]12 BQOFWKZOCNGFEC-BDAKNGLRSA-N 0.000 claims description 5
229930006713 (+)-car-3-ene Natural products 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
125000005907 alkyl ester group Chemical group 0.000 claims description 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229950005228 bromoform Drugs 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
230000009102 absorption Effects 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000005265 dialkylamine group Chemical group 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
OBFSIXAGISHRPF-UHFFFAOYSA-N P.CNC.CNC.CNC Chemical compound P.CNC.CNC.CNC OBFSIXAGISHRPF-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000000749 insecticidal effect Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002728 pyrethroid Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
150000003003 phosphines Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
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 2
PQTDYOQEPYGGHF-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carbaldehyde Chemical compound CC1(C)CC1C=O PQTDYOQEPYGGHF-UHFFFAOYSA-N 0.000 description 1
BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 1
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical group CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
JOHCVVJGGSABQY-UHFFFAOYSA-N carbon tetraiodide Chemical compound IC(I)(I)I JOHCVVJGGSABQY-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical class OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
AZSZCFSOHXEJQE-UHFFFAOYSA-N dibromodifluoromethane Chemical compound FC(F)(Br)Br AZSZCFSOHXEJQE-UHFFFAOYSA-N 0.000 description 1
PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical class Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
ATGNMPQXSQEKAZ-UHFFFAOYSA-N methyl 2-[3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropyl]acetate Chemical compound COC(=O)CC1C(C=C(Cl)Cl)C1(C)C ATGNMPQXSQEKAZ-UHFFFAOYSA-N 0.000 description 1
238000004476 mid-IR spectroscopy Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
FDIOSTIIZGWENY-UHFFFAOYSA-N n-[bis(diethylamino)phosphanyl]-n-ethylethanamine Chemical compound CCN(CC)P(N(CC)CC)N(CC)CC FDIOSTIIZGWENY-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/56—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD79214408A 1978-07-19 1979-07-17 Verfahren fuer die herstellung von zwischenverbindungen fuer die darstellung von cyclopropancarboxylatester DD144912A5 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB7830340		1978-07-19
GB7830339		1978-07-19
GB7833763		1978-08-17

Publications (1)

Publication Number	Publication Date
DD144912A5 true DD144912A5 (de)	1980-11-12

Family

ID=27260571

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79214408A DD144912A5 (de)	1978-07-19	1979-07-17	Verfahren fuer die herstellung von zwischenverbindungen fuer die darstellung von cyclopropancarboxylatester

Country Status (9)

Country	Link
EP (1)	EP0007142B1 (da)
AU (1)	AU528682B2 (da)
BR (1)	BR7904543A (da)
DD (1)	DD144912A5 (da)
DE (1)	DE2962799D1 (da)
DK (1)	DK299979A (da)
HU (1)	HU180524B (da)
IN (1)	IN152613B (da)
SU (1)	SU931101A3 (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4296241A (en) *	1979-07-21	1981-10-20	Bayer Aktiengesellschaft	Preparation of 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid derivatives

1979
- 1979-07-09 EP EP79200379A patent/EP0007142B1/en not_active Expired
- 1979-07-09 DE DE7979200379T patent/DE2962799D1/de not_active Expired
- 1979-07-17 SU SU792788710A patent/SU931101A3/ru active
- 1979-07-17 DD DD79214408A patent/DD144912A5/de unknown
- 1979-07-17 HU HU79SE1946A patent/HU180524B/hu unknown
- 1979-07-17 DK DK299979A patent/DK299979A/da not_active Application Discontinuation
- 1979-07-17 AU AU48982/79A patent/AU528682B2/en not_active Ceased
- 1979-07-17 BR BR7904543A patent/BR7904543A/pt unknown
- 1979-07-17 IN IN515/DEL/79A patent/IN152613B/en unknown

Also Published As

Publication number	Publication date
EP0007142B1 (en)	1982-05-12
IN152613B (da)	1984-02-25
EP0007142A1 (en)	1980-01-23
AU4898279A (en)	1980-01-24
DK299979A (da)	1980-01-20
DE2962799D1 (en)	1982-07-01
AU528682B2 (en)	1983-05-12
BR7904543A (pt)	1980-07-08
HU180524B (en)	1983-03-28
SU931101A3 (ru)	1982-05-23

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DD144912A5 (de)	1980-11-12	Verfahren fuer die herstellung von zwischenverbindungen fuer die darstellung von cyclopropancarboxylatester
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