CH623305A5 - - Google Patents

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Info

Publication number: CH623305A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; radical; sulfone; general formula; desulfonation
Prior art date: 1976-07-28

Application number

CH929377A

Other languages

English (en)

French (fr)

Inventor

Jean-Pierre Decor

Original Assignee

Rhone Poulenc Ind

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.)

1976-07-28

Filing date

1977-07-27

Publication date

1981-05-29

1977-07-27 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1981-05-29 Publication of CH623305A5 publication Critical patent/CH623305A5/fr

Links

VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 27
-1 alkyl radical Chemical class 0.000 claims description 17
150000003457 sulfones Chemical class 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
230000006326 desulfonation Effects 0.000 claims description 9
238000005869 desulfonation reaction Methods 0.000 claims description 9
229930195733 hydrocarbon Natural products 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
239000011591 potassium Substances 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
150000002430 hydrocarbons Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
150000004347 all-trans-retinol derivatives Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 8
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
235000019155 vitamin A Nutrition 0.000 description 6
239000011719 vitamin A Substances 0.000 description 6
229940045997 vitamin a Drugs 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
BHKAWXZKFKVZLK-UHFFFAOYSA-N 2,3-ditert-butyl-6-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(C(C)(C)C)=C1O BHKAWXZKFKVZLK-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
LPQTVHUEAIDBBY-UHFFFAOYSA-N 2,3-ditert-butyl-6-methoxyphenol Chemical compound COC1=CC=C(C(C)(C)C)C(C(C)(C)C)=C1O LPQTVHUEAIDBBY-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
235000019169 all-trans-retinol Nutrition 0.000 description 1
239000011717 all-trans-retinol Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/12—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/22—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH929377A 1976-07-28 1977-07-27 CH623305A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7622992A FR2359821A1 (fr)	1976-07-28	1976-07-28	Perfectionnement au procede de preparation de la vitamine a a partir de sulfones

Publications (1)

Publication Number	Publication Date
CH623305A5 true CH623305A5 (de)	1981-05-29

Family

ID=9176241

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH929377A CH623305A5 (de)	1976-07-28	1977-07-27

Country Status (12)

Country	Link
US (1)	US4175205A (de)
JP (1)	JPS5953903B2 (de)
BE (1)	BE857236A (de)
CA (1)	CA1080242A (de)
CH (1)	CH623305A5 (de)
DE (1)	DE2734172A1 (de)
FR (1)	FR2359821A1 (de)
GB (1)	GB1532915A (de)
HU (1)	HU173649B (de)
IT (1)	IT1085596B (de)
NL (1)	NL187353C (de)
SU (1)	SU722483A3 (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE794872A (fr) *	1972-02-02	1973-08-01	Rhone Poulenc Sa	Nouvelles sulfones derivees de dimethyl-1,5 hexadiene-1,5 ylene
JPS54182007U (de) *	1978-06-13	1979-12-24
US4523042A (en) *	1983-07-29	1985-06-11	Usv Pharmaceutical	Derivatives of alpha-alkyl polyolefinic carboxylic acid useful in the treatment of psoriasis
FR2573074B1 (fr) *	1984-11-13	1987-01-30	Rhone Poulenc Sante	Procede de preparation du retinonitrile
EP0187259B2 (de) *	1985-01-10	1996-05-15	Kuraray Co., Ltd.	Verfahren zur Herstellung von Vitamin A oder seinen Carbonsäureestern und Zwischenprodukte und ihre Verwendung in diesem Verfahren
TW252974B (de) *	1993-03-23	1995-08-01	Takeda Dharm Industry Co Ltd
DE69802465T2 (de) *	1997-05-29	2002-06-27	Sumitomo Chemical Co., Ltd.	Polyalkoholderivate und Verfahren zur Herstellung davon
RU2188193C2 (ru) *	1997-08-25	2002-08-27	Сумитомо Кемикал Компани, Лимитед	Родственное витамину a соединение и способы его получения
DE19926090A1 (de) *	1998-06-12	1999-12-16	Sumitomo Chemical Co	Verfahren und Zwischenprodukt zur Herstellung von Retinal

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES402986A1 (es) *	1971-05-19	1975-04-16	Rhone Poulenc Sa	Procedimiento para la preparacion de compuestos carotenoi- des.
BE794872A (fr) *	1972-02-02	1973-08-01	Rhone Poulenc Sa	Nouvelles sulfones derivees de dimethyl-1,5 hexadiene-1,5 ylene
BE794944A (fr) *	1972-02-04	1973-08-02	Rhone Poulenc Sa	Nouvelles sulfones insaturees comportant une fonction carbonyle
FR2205898A5 (de) *	1972-11-08	1974-05-31	Rhone Poulenc Sa
US3960967A (en) *	1973-09-14	1976-06-01	Hoffmann-La Roche Inc.	Process for producing a sulfone derivative of vitamin A alcohol

1976
- 1976-07-28 FR FR7622992A patent/FR2359821A1/fr active Granted
1977
- 1977-07-20 NL NLAANVRAGE7708083,A patent/NL187353C/xx not_active IP Right Cessation
- 1977-07-25 US US05/818,871 patent/US4175205A/en not_active Expired - Lifetime
- 1977-07-25 JP JP52088461A patent/JPS5953903B2/ja not_active Expired
- 1977-07-26 SU SU772504519A patent/SU722483A3/ru active
- 1977-07-27 BE BE179705A patent/BE857236A/xx not_active IP Right Cessation
- 1977-07-27 CH CH929377A patent/CH623305A5/fr not_active IP Right Cessation
- 1977-07-27 CA CA283,632A patent/CA1080242A/fr not_active Expired
- 1977-07-27 HU HU77RO935A patent/HU173649B/hu not_active IP Right Cessation
- 1977-07-27 GB GB31658/77A patent/GB1532915A/en not_active Expired
- 1977-07-28 DE DE19772734172 patent/DE2734172A1/de active Granted
- 1977-07-28 IT IT26259/77A patent/IT1085596B/it active

Also Published As

Publication number	Publication date
SU722483A3 (ru)	1980-03-15
HU173649B (hu)	1979-07-28
JPS5953903B2 (ja)	1984-12-27
NL187353B (nl)	1991-04-02
NL7708083A (nl)	1978-01-31
US4175205A (en)	1979-11-20
NL187353C (nl)	1991-09-02
BE857236A (fr)	1978-01-27
JPS5315341A (en)	1978-02-13
GB1532915A (en)	1978-11-22
CA1080242A (fr)	1980-06-24
DE2734172C2 (de)	1987-11-05
FR2359821A1 (fr)	1978-02-24
FR2359821B1 (de)	1978-12-15
IT1085596B (it)	1985-05-28
DE2734172A1 (de)	1978-02-02

Legal Events

Date	Code	Title	Description
1995-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
WO1992019620A1 (fr)	1992-11-12	Nouveaux derives de pyrrolo [1, 4]-benzodiazepines, leur procede de preparation et medicaments les contenant
EP0283364A2 (de)	1988-09-21	Mono- oder Diester von Endoethano-9,10-dihydro-9,10-anthracen-dicarboxy-11,11-säure, Verfahren zur Herstellung und Anwendung um symmetrische oder asymmetrische Methyliden-Malonate herzustellen
CA1080242A (fr)	1980-06-24	Procede de preparation de la vitamine a a partir de sulfones
FR2921921A1 (fr)	2009-04-10	Procede de synthese de composes polyhydroxystilbeniques.
MC1175A1 (fr)	1978-09-25	Derives polyeniques
EP0267828A1 (de)	1988-05-18	Polyfluorierte Verbindungen und Verfahren zu deren Herstellung
EP0171320B1 (de)	1987-10-28	Herstellungsverfahren von ungesättigten, in alpha-chlorierten Verbindungen von zwei in beta-Stellung elektronenanziehenden Gruppen
EP0486385A1 (de)	1992-05-20	Imidazol-Derivate, Verfahren zu deren Herstellung und diese enthaltende Zusammenstellungen
EP0127536B1 (de)	1987-01-21	Verfahren zur Herstellung von alpha-delta-diethylenischen Carbonylverbindungen
CA1261319A (fr)	1989-09-26	Procede de preparation de derives n-methyles de l'ergoline
EP3592753B1 (de)	2022-02-16	Neuartige zusammensetzung von 7,9-dodecadienyl-1-acetat-isomeren und verfahren zur herstellung davon
CA1278316C (fr)	1990-12-27	Methyl-3 alkoxy-1 hexatriene-1,3,5 et leurs utilisations pour la production d'aldehydes polyeniques
EP0146439B1 (de)	1987-05-20	Herstellungsverfahren von acetylenischen Verbindungen, so erhaltene acetylenische Verbindungen und ihre Anwendung
CA1227804A (fr)	1987-10-06	Derives de la 4,4-dimethyl tetrahydro-2-pyran-2-one, leur procede de preparation et leur application a la synthese de derives cyclopropaniques
EP0314575B1 (de)	1992-04-15	Verfahren zur Herstellung von Retinal
EP0385874A1 (de)	1990-09-05	Funktionalisierung in Stellung (n+1) von in Stellung n und (n+2) disubstituierten Arylderivaten
FR2663023A1 (fr)	1991-12-13	Procede de transformation de n-oxydes d'amines tertiaires en aldehydes.
EP0579991B1 (de)	1998-09-16	Verfahren zur Herstellung eines bicyclischen Decalinketons
EP0172066B1 (de)	1987-09-30	Herstellungsverfahren von in alpha-Stellung einer elektronenanziehenden Gruppe halogenierten Verbindungen
EP0060767B1 (de)	1984-06-27	Verfahren zur Herstellung von delta-äthylenisch ungesättigten Carbonylverbindungen
FR2529549A1 (fr)	1984-01-06	Oxime-ethers d'eburnane, procede pour leur preparation et compositions pharmaceutiques qui les contiennent
EP0348254B1 (de)	1993-06-23	Verfahren zur Herstellung von norpyrethroiden Verbindungen
CH622247A5 (en)	1981-03-31	Process for the preparation of prostaglandin A2 and of certain of its derivatives
EP0671375A1 (de)	1995-09-13	Verfahren zur Herstellung von 2,6-Bis(trifluoromethyl)benzylalkohol
EP0442258A2 (de)	1991-08-21	Verfahren zur Herstellung einer mehrfach ungesättigten Verbindung