IL30905A - Process for preparing a cyclopropanecarboxylic acid - Google Patents

Process for preparing a cyclopropanecarboxylic acid

Info

Publication number: IL30905A
Authority: IL; Israel
Prior art keywords: salt; alkali; process according; trans; acid
Prior art date: 1967-11-10

Application number

IL30905A

Other languages

English (en)

Other versions

IL30905A0 (en

Original Assignee

Roussel Uclaf

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.)

1967-11-10

Filing date

1968-10-21

Publication date

1972-08-30

1968-10-21 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1968-12-26 Publication of IL30905A0 publication Critical patent/IL30905A0/xx

1972-08-30 Publication of IL30905A publication Critical patent/IL30905A/en

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
238000000746 purification Methods 0.000 claims description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 7
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
-1 alkyl radical Chemical class 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 5
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
UIWNHGWOYRFCSF-KTERXBQFSA-N (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound COC(=O)C(\C)=C\[C@@H]1[C@@H](C(O)=O)C1(C)C UIWNHGWOYRFCSF-KTERXBQFSA-N 0.000 claims description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
UIWNHGWOYRFCSF-UHFFFAOYSA-N Pyrethric acid Natural products COC(=O)C(C)=CC1C(C(O)=O)C1(C)C UIWNHGWOYRFCSF-UHFFFAOYSA-N 0.000 claims description 2
239000007859 condensation product Substances 0.000 claims description 2
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 2
229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
150000008046 alkali metal hydrides Chemical class 0.000 claims 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000284 extract Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
239000000047 product Substances 0.000 description 4
229960000948 quinine Drugs 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 3
241000786363 Rhampholeon spectrum Species 0.000 description 3
239000003513 alkali Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
235000001258 Cinchona calisaya Nutrition 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
DZWLWXNBYUMTSL-UHFFFAOYSA-N (1-methoxy-1-oxopropan-2-yl)phosphonic acid Chemical compound COC(=O)C(C)P(O)(O)=O DZWLWXNBYUMTSL-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
229910014570 C—OH Inorganic materials 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
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
241001342522 Vampyrum spectrum Species 0.000 description 1
VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical class [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000002983 circular dichroism Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000003197 gene knockdown Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
UWCWSEMVQFWUHB-UHFFFAOYSA-N iodophosphonic acid Chemical compound OP(O)(I)=O UWCWSEMVQFWUHB-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
229940070846 pyrethrins Drugs 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/16—Saturated compounds containing —CHO groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL30905A 1967-11-10 1968-10-21 Process for preparing a cyclopropanecarboxylic acid IL30905A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR127745		1967-11-10

Publications (2)

Publication Number	Publication Date
IL30905A0 IL30905A0 (en)	1968-12-26
IL30905A true IL30905A (en)	1972-08-30

Family

ID=8641542

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL30905A IL30905A (en)	1967-11-10	1968-10-21	Process for preparing a cyclopropanecarboxylic acid

Country Status (13)

Country	Link
AT (1)	AT286960B (pl)
CH (1)	CH498797A (pl)
CS (1)	CS200161B2 (pl)
DE (2)	DE1817881A1 (pl)
DK (1)	DK144941C (pl)
FR (1)	FR1579476A (pl)
GB (2)	GB1246814A (pl)
IL (1)	IL30905A (pl)
NL (2)	NL6815987A (pl)
PL (1)	PL69854B1 (pl)
SE (1)	SE353709B (pl)
SU (1)	SU423290A3 (pl)
YU (1)	YU34271B (pl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2730515A1 (de) *	1977-07-06	1979-01-18	Bayer Ag	Substituierte phenoxybenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
US4296241A (en) *	1979-07-21	1981-10-20	Bayer Aktiengesellschaft	Preparation of 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid derivatives

0
- NL NL133054D patent/NL133054C/xx active
1967
- 1967-11-10 FR FR127745A patent/FR1579476A/fr not_active Expired
1968
- 1968-10-21 IL IL30905A patent/IL30905A/en unknown
- 1968-11-01 DK DK530268A patent/DK144941C/da not_active IP Right Cessation
- 1968-11-01 CH CH1633668A patent/CH498797A/fr not_active IP Right Cessation
- 1968-11-05 DE DE19681817881 patent/DE1817881A1/de active Granted
- 1968-11-05 DE DE19681807091 patent/DE1807091B2/de active Granted
- 1968-11-06 SU SU1283233A patent/SU423290A3/ru active
- 1968-11-06 YU YU2608/68A patent/YU34271B/xx unknown
- 1968-11-08 PL PL1968129971A patent/PL69854B1/pl unknown
- 1968-11-08 SE SE15201/68A patent/SE353709B/xx unknown
- 1968-11-08 NL NL6815987A patent/NL6815987A/xx unknown
- 1968-11-11 GB GB4197/71A patent/GB1246814A/en not_active Expired
- 1968-11-11 AT AT1096168A patent/AT286960B/de not_active IP Right Cessation
- 1968-11-11 GB GB53375/68A patent/GB1246813A/en not_active Expired
- 1968-11-11 CS CS687671A patent/CS200161B2/cs unknown

Also Published As

Publication number	Publication date
GB1246814A (en)	1971-09-22
DK144941C (da)	1982-11-29
PL69854B1 (pl)	1973-10-31
AT286960B (de)	1971-01-11
CH498797A (fr)	1970-11-15
SU423290A3 (pl)	1974-04-05
DK144941B (da)	1982-07-12
SE353709B (pl)	1973-02-12
YU34271B (en)	1979-04-30
YU260868A (en)	1978-10-31
NL133054C (pl)
NL6815987A (pl)	1969-05-13
GB1246813A (en)	1971-09-22
DE1807091A1 (de)	1969-10-02
DE1817881A1 (de)	1973-03-08
DE1817881B2 (pl)	1978-11-23
CS200161B2 (en)	1980-08-29
DE1807091B2 (de)	1973-04-19
FR1579476A (pl)	1969-08-29
IL30905A0 (en)	1968-12-26
DE1807091C3 (pl)	1973-11-08
DE1817881C3 (pl)	1979-08-02

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US3660542A (en)	1972-05-02	Alkylbenzoylcarbinol phosphate esters
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US3163669A (en)	1964-12-29	Unsaturated carboxylic acid esters containing phosphorus
US2664437A (en)	1953-12-29	O-(2-chloro-4-nitrophenyl) o,o dimethyl thiophosphate
US2681920A (en)	1954-06-22	Preparation of phosphonates
IL30905A (en)	1972-08-30	Process for preparing a cyclopropanecarboxylic acid
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US2722479A (en)	1955-11-01	Triisooctyl phosphite and herbicides containing same
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US2980692A (en)	1961-04-18	3-indolemethanephosphonic acid and its salts and preparation thereof
James	1911	CLXXXIV.—The β-chlorocinnamic acids
US5847185A (en)	1998-12-08	C-15 phosphonate reagent compositions and methods of synthesizing the same
US3775519A (en)	1973-11-27	Preparation of phosphoroamido-thionate by ketene acylation
JPS6136288A (ja)	1986-02-20	塩素置換ホスホリルメチルカルボニル誘導体の製造方法およびその製造のための新規な中間体