CA1120486A - Intermediaire dans la synthese de l'acide (ir cis)-caronaldehydique - Google Patents

Intermediaire dans la synthese de l'acide (ir cis)-caronaldehydique

Info

Publication number: CA1120486A
Authority: CA; Canada
Prior art keywords: acid; cis; preparation; process according; compound
Prior art date: 1977-08-09
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

CA000372092A

Other languages

English (en)

Inventor

Steven A. Roman

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.)

1977-08-09

Filing date

1981-03-02

Publication date

1982-03-23

1977-08-09 Priority claimed from US05/823,233 external-priority patent/US4132717A/en

1981-03-02 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1981-03-02 Priority to CA000372092A priority Critical patent/CA1120486A/fr

1982-03-23 Application granted granted Critical

1982-03-23 Publication of CA1120486A publication Critical patent/CA1120486A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims abstract description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 3
238000006210 cyclodehydration reaction Methods 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 2
BKUHNVYPRVILOX-BQBZGAKWSA-N (1r,3s)-2,2-dimethyl-3-(2-oxopropyl)cyclopropane-1-carboxylic acid Chemical compound CC(=O)C[C@H]1[C@@H](C(O)=O)C1(C)C BKUHNVYPRVILOX-BQBZGAKWSA-N 0.000 claims 1
-1 bicyclic enol lactone Chemical class 0.000 abstract description 6
230000000749 insecticidal effect Effects 0.000 abstract description 2
239000002728 pyrethroid Substances 0.000 abstract description 2
239000002917 insecticide Substances 0.000 abstract 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
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
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 description 2
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
BKUHNVYPRVILOX-UHFFFAOYSA-N 2,2-dimethyl-3-(2-oxopropyl)cyclopropane-1-carboxylic acid Chemical compound CC(=O)CC1C(C(O)=O)C1(C)C BKUHNVYPRVILOX-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241000428533 Rhis Species 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229940022682 acetone Drugs 0.000 description 1
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000004458 analytical method Methods 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
229930006737 car-3-ene Natural products 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007858 starting material 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
238000001665 trituration Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Landscapes

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

CA000372092A 1977-08-09 1981-03-02 Intermediaire dans la synthese de l'acide (ir cis)-caronaldehydique Expired CA1120486A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000372092A CA1120486A (fr)	1977-08-09	1981-03-02	Intermediaire dans la synthese de l'acide (ir cis)-caronaldehydique

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/823,233 US4132717A (en)	1977-08-09	1977-08-09	Enol lactone intermediate for the preparation of (1R,cis)-caronaldehydic acid
US823,233		1977-08-09
CA306,820A CA1110256A (fr)	1977-08-09	1978-07-05	Obtention d'acides (1r,cis)-caronaldehydiques
CA000372092A CA1120486A (fr)	1977-08-09	1981-03-02	Intermediaire dans la synthese de l'acide (ir cis)-caronaldehydique

Publications (1)

Publication Number	Publication Date
CA1120486A true CA1120486A (fr)	1982-03-23

Family

ID=27165738

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000372092A Expired CA1120486A (fr)	1977-08-09	1981-03-02	Intermediaire dans la synthese de l'acide (ir cis)-caronaldehydique

Country Status (1)

Country	Link
CA (1)	CA1120486A (fr)

1981
- 1981-03-02 CA CA000372092A patent/CA1120486A/fr not_active Expired

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Legal Events

Date	Code	Title	Description
1999-03-23	MKEX	Expiry