IL31082A - Derivatives of heptenoic acid - Google Patents

Derivatives of heptenoic acid

Info

Publication number: IL31082A
Authority: IL; Israel
Prior art keywords: acid; aryl; lower alkyl; halogen; group
Prior art date: 1964-05-26

Application number

IL31082A

Other languages

English (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.)

1964-05-26

Filing date

1965-05-13

Publication date

1969-05-28

1965-05-13 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1969-05-28 Publication of IL31082A publication Critical patent/IL31082A/en

Links

YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical class CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 title 1
125000003118 aryl group Chemical group 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 14
-1 alkyl halogen Chemical class 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
150000004702 methyl esters Chemical class 0.000 claims description 5
125000005907 alkyl ester group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
AUGKLUNRHYPDAM-UHFFFAOYSA-N 3-methylbut-2-enenitrile Chemical compound CC(C)=CC#N AUGKLUNRHYPDAM-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
238000009432 framing Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
125000004391 aryl sulfonyl group Chemical group 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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 3
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 2
150000003457 sulfones Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000005362 aryl sulfone group Chemical group 0.000 description 1
210000000941 bile Anatomy 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
UTXVCHVLDOLVPC-UHFFFAOYSA-N ethyl 3-methylbut-2-enoate Chemical compound CCOC(=O)C=C(C)C UTXVCHVLDOLVPC-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000003106 haloaryl group Chemical group 0.000 description 1
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
YWOITFUKFOYODT-UHFFFAOYSA-N methanol;sodium Chemical compound [Na].OC YWOITFUKFOYODT-UHFFFAOYSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
- C07C317/04—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton

Landscapes

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

IL31082A 1964-05-26 1965-05-13 Derivatives of heptenoic acid IL31082A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR975870A FR1483715A (fr)	1964-05-26	1964-05-26	Nouvelles aryl sulfones substituées insaturées et procédé de préparation
FR975871A FR1488209A (fr)	1964-05-26	1964-05-26	Procédé de préparation de dérivés du cyclopropane et produits obtenus au cours de ce procédé

Publications (1)

Publication Number	Publication Date
IL31082A true IL31082A (en)	1969-05-28

Family

ID=26207890

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
IL31082A IL31082A (en)	1964-05-26	1965-05-13	Derivatives of heptenoic acid
IL23530A IL23530A (en)	1964-05-26	1965-05-13	Process for the preparation of transchrysanthemumic acid
IL31081A IL31081A (en)	1964-05-26	1965-05-13	Substituted aryl sulfones

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
IL23530A IL23530A (en)	1964-05-26	1965-05-13	Process for the preparation of transchrysanthemumic acid
IL31081A IL31081A (en)	1964-05-26	1965-05-13	Substituted aryl sulfones

Country Status (10)

Country	Link
US (2)	US3445499A (fr)
BE (2)	BE698126A (fr)
BR (1)	BR6569889D0 (fr)
CH (1)	CH436246A (fr)
DE (1)	DE1289046B (fr)
DK (1)	DK121855B (fr)
FR (2)	FR1488209A (fr)
GB (1)	GB1069038A (fr)
IL (3)	IL31082A (fr)
SE (1)	SE312137B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3997586A (en) *	1967-08-22	1976-12-14	Roussel-Uclaf	Cyclopropanecarboxylic acids and esters
FR92123E (fr) *	1966-10-12	1968-09-27	Rhone Poulenc Sa	Nouveau procédé de préparation de l'acide chrysanthémique
JPS5220473B1 (fr) *	1970-06-29	1977-06-03
BE794874A (fr) *	1972-02-02	1973-08-01	Rhone Poulenc Sa	Nouvelles sulfones isopreniques a fonctions ethers
FR2179499B1 (fr) *	1972-04-10	1977-08-05	Rhone Poulenc Ind
FR2181113A5 (fr) *	1972-04-17	1973-11-30	Rhone Poulenc Sa
DE2926671A1 (de) *	1979-07-02	1981-01-15	Bayer Ag	Verfahren zur herstellung von cyclopropan-carbonsaeure-derivaten sowie neue zwischenprodukte hierfuer und verfahren zu deren herstellung
DE2936038A1 (de) *	1979-09-06	1981-03-26	Bayer Ag, 51373 Leverkusen	Verfahren zur herstellung von 1-aminocyclopropan-carbonsaeure und deren derivaten
FR2479192A1 (fr) *	1980-03-28	1981-10-02	Roussel Uclaf	Procede de preparation de derives cyclopropaniques tetra-substitues
FR2479213A1 (fr) *	1980-03-28	1981-10-02	Roussel Uclaf	Procede de preparation d'acide pentenoique possedant une fonction aldehyde
FR2490633A1 (fr)	1980-09-24	1982-03-26	Roussel Uclaf	Procede de preparation de derives d'acides cyclopropane carboxyliques porteurs d'une fonction aldehyde
US5095136A (en) *	1990-08-27	1992-03-10	E. R. Squibb & Sons, Inc.	Method for preparing isoprenoid cyclopropane 1,1-dicarboxylates and derivatives thereof and novel intermediates
US5157146A (en) *	1990-08-27	1992-10-20	E. R. Squibb & Sons, Inc.	Method for preparing isoprenoid cyclopropane 1,1-dicarboxylates

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2435552A (en) *	1945-05-04	1948-02-03	Resinous Prod & Chemical Co	Addition products of acrylonitrile and aryl sulfones and process for preparing same
FR1269127A (fr) *	1960-06-20	1961-08-11	Rhone Poulenc Sa	Procédé de préparation de l'acide chrysanthémique

1964
- 1964-05-26 FR FR975871A patent/FR1488209A/fr not_active Expired
- 1964-05-26 FR FR975870A patent/FR1483715A/fr not_active Expired
1965
- 1965-05-10 US US454691A patent/US3445499A/en not_active Expired - Lifetime
- 1965-05-12 CH CH658065A patent/CH436246A/fr unknown
- 1965-05-13 IL IL31082A patent/IL31082A/en unknown
- 1965-05-13 IL IL23530A patent/IL23530A/xx unknown
- 1965-05-13 IL IL31081A patent/IL31081A/en unknown
- 1965-05-17 DK DK246265AA patent/DK121855B/da unknown
- 1965-05-19 SE SE6566/65A patent/SE312137B/xx unknown
- 1965-05-25 GB GB22170/65A patent/GB1069038A/en not_active Expired
- 1965-05-25 BR BR169889/65A patent/BR6569889D0/pt unknown
- 1965-05-25 DE DER40714A patent/DE1289046B/de active Pending
1967
- 1967-05-08 BE BE698126D patent/BE698126A/xx not_active IP Right Cessation
- 1967-06-22 BE BE700357D patent/BE700357A/xx not_active IP Right Cessation
1971
- 1971-03-22 US US27592D patent/USRE27592E/en not_active Expired

Also Published As

Publication number	Publication date
BR6569889D0 (pt)	1973-12-26
DE1289046B (de)	1969-02-13
CH436246A (fr)	1967-05-31
IL31081A (en)	1969-05-28
SE312137B (fr)	1969-07-07
USRE27592E (en)	1973-03-06
BE698126A (fr)	1967-10-16
BE700357A (fr)	1967-12-01
FR1483715A (fr)	1967-06-09
US3445499A (en)	1969-05-20
FR1488209A (fr)	1967-07-13
IL23530A (en)	1969-01-29
GB1069038A (en)	1967-05-17
DK121855B (da)	1971-12-13

Publication	Publication Date	Title
US2553771A (en)	1951-05-22	Method of preparing n-trichloromethylthioimides
IL31082A (en)	1969-05-28	Derivatives of heptenoic acid
US4144397A (en)	1979-03-13	Preparation of 2-aryl-propionic acids by direct coupling utilizing a mixed magnesium halide complex
JPH0134219B2 (fr)	1989-07-18
US2710862A (en)	1955-06-14	Production of diaryldiazomethanes
US3953531A (en)	1976-04-27	Alkylhydroquinone and process for producing the same
US3830862A (en)	1974-08-20	Reactions involving carbon tetrahalides with sulfones
US2493126A (en)	1950-01-03	Manufacture of chlorinated phenoxy compounds
EP0105664B1 (fr)	1986-11-20	Procédé pour la préparation d'acide 3-carboxy-1-méthyl-2-acétique et des sels de métal alkalin
US3870744A (en)	1975-03-11	Process for oxygen-alkylation of sterically hindered phenols
US3136800A (en)	1964-06-09	Method for producing hydroxythiobenzoic acids and esters thereof
JPS60246382A (ja)	1985-12-06	アルキル２‐（２‐アシルアミドチアゾール‐４‐イル）‐２‐ブテノエード類およびそれらの製法
US2563375A (en)	1951-08-07	5-aminoisophthaloylacetonitrile
JPH0761993B2 (ja)	1995-07-05	アジドスルホニル安息香酸の製造法
SU1205756A3 (ru)	1986-01-15	Способ получени 1,1-дихлор-4-метилпентадиенов
US2489927A (en)	1949-11-29	Preparation of intermediates for synthesis of amino acids
US4339601A (en)	1982-07-13	Terephthalic acid derivatives and process for preparing them
EP0661263A2 (fr)	1995-07-05	Procédé pour la préparation de 2,4,5 tribromopyrrole-3-carbonitrile
US4252979A (en)	1981-02-24	Terephthalic acid derivatives
US2704290A (en)	1955-03-15	New class of phthalide compounds and methods of preparing the same
JPS63280084A (ja)	1988-11-17	１−アルキル−３−カルボキシ−４−シンノロン類の製造方法
KR860001312B1 (ko)	1986-09-13	말론산 유도체의 제조방법
US3027406A (en)	1962-03-27	3-hydroxy-3-biphenylylheptanoic acid
KR100359503B1 (ko)	2002-10-31	방향족 프로피온산 유도체의 제조방법
KR910003636B1 (ko)	1991-06-07	벤조페논 옥심화합물의 제조방법