CA1155455A - Produits intermediaires dans la preparation d'esters cyclopropanecarboxylates et methode d'obtention - Google Patents

Produits intermediaires dans la preparation d'esters cyclopropanecarboxylates et methode d'obtention

Info

Publication number: CA1155455A
Authority: CA; Canada
Prior art keywords: formula; iii; preparation; compound; intermediates
Prior art date: 1978-07-19
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

Application number

CA000331942A

Other languages

English (en)

Inventor

Johannes L.M. Syrier

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Canada Ltd

Original Assignee

Shell Canada 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.)

1978-07-19

Filing date

1979-07-17

Publication date

1983-10-18

1979-07-17 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1983-10-18 Application granted granted Critical

1983-10-18 Publication of CA1155455A publication Critical patent/CA1155455A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title claims description 7
239000000543 intermediate Substances 0.000 title abstract description 8
238000004519 manufacturing process Methods 0.000 title abstract description 3
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 10
239000007858 starting material Substances 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
BQOFWKZOCNGFEC-BDAKNGLRSA-N (+)-Delta3-carene Chemical compound C1C(C)=CC[C@H]2C(C)(C)[C@@H]12 BQOFWKZOCNGFEC-BDAKNGLRSA-N 0.000 claims abstract 3
229930006713 (+)-car-3-ene Natural products 0.000 claims abstract 3
BQOFWKZOCNGFEC-UHFFFAOYSA-N Delta3-Carene Natural products C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims abstract 3
-1 cyclopropane compound Chemical class 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
150000004967 organic peroxy acids Chemical class 0.000 claims description 2
239000002728 pyrethroid Substances 0.000 abstract description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 3
229910052794 bromium Inorganic materials 0.000 abstract description 3
229910052801 chlorine Inorganic materials 0.000 abstract description 3
239000000460 chlorine Substances 0.000 abstract description 3
239000002917 insecticide Substances 0.000 abstract description 2
150000002148 esters Chemical class 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000000749 insecticidal effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
GOKCJCODOLGYQD-UHFFFAOYSA-N 4,6-dichloro-2-imidazol-1-ylpyrimidine Chemical compound ClC1=CC(Cl)=NC(N2C=NC=C2)=N1 GOKCJCODOLGYQD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000000047 product Substances 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-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
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001942 cyclopropanes Chemical class 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
230000007775 late Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/16—Acetic acid esters of dihydroxylic compounds

Landscapes

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

CA000331942A 1978-07-19 1979-07-17 Produits intermediaires dans la preparation d'esters cyclopropanecarboxylates et methode d'obtention Expired CA1155455A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB30.335/78		1978-07-19
GB7830335		1978-07-19

Publications (1)

Publication Number	Publication Date
CA1155455A true CA1155455A (fr)	1983-10-18

Family

ID=10498512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000331942A Expired CA1155455A (fr)	1978-07-19	1979-07-17	Produits intermediaires dans la preparation d'esters cyclopropanecarboxylates et methode d'obtention

Country Status (8)

Country	Link
JP (1)	JPS5543070A (fr)
BE (1)	BE877744A (fr)
CA (1)	CA1155455A (fr)
CH (1)	CH641144A5 (fr)
DE (1)	DE2928834A1 (fr)
DK (1)	DK300579A (fr)
FR (1)	FR2431484A1 (fr)
NL (1)	NL7905550A (fr)

1979
- 1979-07-17 DE DE19792928834 patent/DE2928834A1/de not_active Withdrawn
- 1979-07-17 CH CH664579A patent/CH641144A5/de not_active IP Right Cessation
- 1979-07-17 DK DK300579A patent/DK300579A/da not_active Application Discontinuation
- 1979-07-17 NL NL7905550A patent/NL7905550A/nl not_active Application Discontinuation
- 1979-07-17 BE BE0/196337A patent/BE877744A/fr not_active IP Right Cessation
- 1979-07-17 FR FR7918454A patent/FR2431484A1/fr active Granted
- 1979-07-17 CA CA000331942A patent/CA1155455A/fr not_active Expired
- 1979-07-17 JP JP8995679A patent/JPS5543070A/ja active Pending

Also Published As

Publication number	Publication date
BE877744A (fr)	1980-01-17
JPS5543070A (en)	1980-03-26
DE2928834A1 (de)	1980-01-31
FR2431484B1 (fr)	1981-09-04
CH641144A5 (en)	1984-02-15
NL7905550A (nl)	1980-01-22
DK300579A (da)	1980-01-20
FR2431484A1 (fr)	1980-02-15

Legal Events

Date	Code	Title	Description
2000-10-18	MKEX	Expiry

Publication	Publication Date	Title
DENNEY et al.	1962	The Preparation and Reactions of Some Halophosphoranes1
US4772727A (en)	1988-09-20	Method of producing enantiomerically pure R-(+)-alpha-lipoic acid and S-(-)a
EP0022162A1 (fr)	1981-01-14	Procédé de préparation d'hydroxy-4 cyclopenténones disubstituées; cyclopentènediones et hydroxy-4 cyclopenténones monosubstituées
EP3556743B1 (fr)	2020-12-09	Procédé de préparation de (9e,11z)-9, 11-hexadécadiénal
DK142765B (da)	1981-01-19	Fremgangsmåde til fremstilling af optisk aktive estere af chrysanthemsyre.
HU185330B (en)	1985-01-28	Process for preparing /+/-4-substituted-2-indazoles
CA1155455A (fr)	1983-10-18	Produits intermediaires dans la preparation d'esters cyclopropanecarboxylates et methode d'obtention
JPS6025952A (ja)	1985-02-08	光学活性２，２−ジメチルシクロプロパン−１−カルボン酸誘導体の製造法
US3281440A (en)	1966-10-25	Fluorinated vitamin a compounds
US4083855A (en)	1978-04-11	Method for producing a γ-lactone
US4107181A (en)	1978-08-15	Useful prostaglandin intermediates
GB2026483A (en)	1980-02-06	Cyclopropane derivatives
USH49H (en)	1986-04-01	Process for producing 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates
CA1119617A (fr)	1982-03-09	Produits intermediaires de la preparation d'esters cyclopropanecarboxylates, et procede pour leur fabrication
US4697032A (en)	1987-09-29	Process for the preparation of 1-bromoethyl hydrocarbonyl carbonates and new 1-bromoethyl hydrocarbonyl carbonates
JPH0759562B2 (ja)	1995-06-28	１，３−ジアルキルピラゾール−５−カルボン酸エステル類の製造法
JPS647065B2 (fr)	1989-02-07
JPS6160822B2 (fr)	1986-12-23
EP0002556B1 (fr)	1981-11-25	Nouvel intermédiaire pour la préparation d'esters cyclopropane carboxyliques et procédé pour sa préparation
US5225605A (en)	1993-07-06	Process for producing pyrethrolone and its intermediate compound
EP0002852B1 (fr)	1981-11-25	Nouvel intermédiaire dans la préparation d'esters cyclopropanecarboxyliques et procédé pour sa préparation
FR2543547A1 (fr)	1984-10-05	Nouveaux mono et bis-chlorosulfonates, utiles notamment comme intermediaires, et leurs procedes de preparation
GB2025962A (en)	1980-01-30	Cyclopropane Derivatives
US4058567A (en)	1977-11-15	Cyclopentene sulfoxides
US4052434A (en)	1977-10-04	Prostaglandin intermediates