CH641142A5 - (1R,-cis)-1-(2-Formyl-3,3-dimethylcyclopropyl)-3-oxo-2-butyl acetate and a process for its preparation - Google Patents

(1R,-cis)-1-(2-Formyl-3,3-dimethylcyclopropyl)-3-oxo-2-butyl acetate and a process for its preparation Download PDF

Info

Publication number: CH641142A5
Authority: CH; Switzerland
Prior art keywords: cis; oxo; formyl; formula; butyl acetate
Prior art date: 1978-07-19

Application number

CH665279A

Other languages

German (de)

English (en)

Inventor

Johannes Leopold Marie 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

1984-02-15

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

1984-02-15 Publication of CH641142A5 publication Critical patent/CH641142A5/de

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 5
-1 Cyclopropane compound Chemical class 0.000 claims description 7
239000012345 acetylating agent Substances 0.000 claims description 3
239000012433 hydrogen halide Substances 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
QTCRRHQJENNMJD-JKIOLJMWSA-N [1-[(1r,3s)-3-formyl-2,2-dimethylcyclopropyl]-3-oxobutan-2-yl] acetate Chemical compound CC(=O)OC(C(C)=O)C[C@@H]1[C@H](C=O)C1(C)C QTCRRHQJENNMJD-JKIOLJMWSA-N 0.000 claims 2
150000001875 compounds Chemical class 0.000 description 7
BQOFWKZOCNGFEC-BDAKNGLRSA-N (+)-Delta3-carene Chemical compound C1C(C)=CC[C@H]2C(C)(C)[C@@H]12 BQOFWKZOCNGFEC-BDAKNGLRSA-N 0.000 description 4
229930006713 (+)-car-3-ene Natural products 0.000 description 4
BQOFWKZOCNGFEC-UHFFFAOYSA-N Delta3-Carene Natural products C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
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 4
239000000203 mixture Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
230000000749 insecticidal effect Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000002728 pyrethroid Substances 0.000 description 3
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 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
LLMLSUSAKZVFOA-NJGYIYPDSA-N (1r,3r)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(O)=O LLMLSUSAKZVFOA-NJGYIYPDSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
229910014570 C—OH Inorganic materials 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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
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 1
238000001311 chemical methods and process Methods 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring 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
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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/185—Saturated compounds containing keto groups bound to acyclic carbon atoms containing —CHO groups

Landscapes

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

CH665279A 1978-07-19 1979-07-17 (1R,-cis)-1-(2-Formyl-3,3-dimethylcyclopropyl)-3-oxo-2-butyl acetate and a process for its preparation CH641142A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7830373		1978-07-19

Publications (1)

Publication Number	Publication Date
CH641142A5 true CH641142A5 (en)	1984-02-15

Family

ID=10498526

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH665279A CH641142A5 (en)	1978-07-19	1979-07-17	(1R,-cis)-1-(2-Formyl-3,3-dimethylcyclopropyl)-3-oxo-2-butyl acetate and a process for its preparation

Country Status (8)

Country	Link
JP (1)	JPS5515491A (fr)
BE (1)	BE877751A (fr)
CA (1)	CA1147347A (fr)
CH (1)	CH641142A5 (fr)
DE (1)	DE2928839A1 (fr)
DK (1)	DK300479A (fr)
FR (1)	FR2431483A1 (fr)
NL (1)	NL7905551A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0463246B1 (fr) *	1990-06-25	1996-02-28	Showa Shell Sekiyu Kabushiki Kaisha	Procédé pour la préparation de copolyesters aromatiques

1979
- 1979-07-17 BE BE0/196344A patent/BE877751A/fr not_active IP Right Cessation
- 1979-07-17 DE DE19792928839 patent/DE2928839A1/de not_active Withdrawn
- 1979-07-17 DK DK300479A patent/DK300479A/da not_active Application Discontinuation
- 1979-07-17 FR FR7918461A patent/FR2431483A1/fr active Granted
- 1979-07-17 NL NL7905551A patent/NL7905551A/nl not_active Application Discontinuation
- 1979-07-17 CA CA000331944A patent/CA1147347A/fr not_active Expired
- 1979-07-17 CH CH665279A patent/CH641142A5/de not_active IP Right Cessation
- 1979-07-17 JP JP8995579A patent/JPS5515491A/ja active Pending

Also Published As

Publication number	Publication date
BE877751A (fr)	1980-01-17
DK300479A (da)	1980-01-20
FR2431483B1 (fr)	1984-02-03
DE2928839A1 (de)	1980-01-31
CA1147347A (fr)	1983-05-31
FR2431483A1 (fr)	1980-02-15
JPS5515491A (en)	1980-02-02
NL7905551A (nl)	1980-01-22

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Legal Events

Date	Code	Title	Description
1985-03-29	PL	Patent ceased
2024-10-31	PL	Patent ceased