LU80394A1 - Procede de monoetherification selective de la pyrocatechine - Google Patents

Procede de monoetherification selective de la pyrocatechine Download PDF

Info

Publication number: LU80394A1
Authority: LU; Luxembourg
Prior art keywords: pyrocatechin; mole; starting; methallyl chloride; pyrocatechol
Prior art date: 1977-10-20

Application number

LU80394A

Other languages

English (en)

French (fr)

Inventor

M Rakoutz

Original Assignee

Philagro Sa

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.)

1977-10-20

Filing date

1978-10-19

Publication date

1980-05-07

1978-10-19 Application filed by Philagro Sa filed Critical Philagro Sa

1980-05-07 Publication of LU80394A1 publication Critical patent/LU80394A1/fr

Links

YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 title claims description 86
238000000034 method Methods 0.000 title claims description 25
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 claims description 25
AAXBKJXGVXNSHI-UHFFFAOYSA-N 2-(2-methylprop-2-enoxy)phenol Chemical compound CC(=C)COC1=CC=CC=C1O AAXBKJXGVXNSHI-UHFFFAOYSA-N 0.000 claims description 15
229910052783 alkali metal Inorganic materials 0.000 claims description 8
239000000010 aprotic solvent Substances 0.000 claims description 8
150000001340 alkali metals Chemical class 0.000 claims description 7
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
-1 alkali metal acid carbonate Chemical class 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 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 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims 2
239000011591 potassium Substances 0.000 claims 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
230000029936 alkylation Effects 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001555 benzenes Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
230000009466 transformation Effects 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
150000005205 dihydroxybenzenes Chemical class 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
238000006266 etherification reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000016936 Dendrocalamus strictus Nutrition 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
125000000746 allylic group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
230000001174 ascending effect Effects 0.000 description 1
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
DHAFIDRKDGCXLV-UHFFFAOYSA-N n,n-dimethylformamide;1-methylpyrrolidin-2-one Chemical compound CN(C)C=O.CN1CCCC1=O DHAFIDRKDGCXLV-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000004028 organic sulfates Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
125000003186 propargylic group Chemical group 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000029305 taxis Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups

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)
Catalysts (AREA)

LU80394A 1977-10-20 1978-10-19 Procede de monoetherification selective de la pyrocatechine LU80394A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7732340		1977-10-20
FR7732340A FR2406622A1 (fr)	1977-10-20	1977-10-20	Procede de monoetherification selective de la pyrocatechine

Publications (1)

Publication Number	Publication Date
LU80394A1 true LU80394A1 (fr)	1980-05-07

Family

ID=9196982

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU80394A LU80394A1 (fr)	1977-10-20	1978-10-19	Procede de monoetherification selective de la pyrocatechine

Country Status (20)

Country	Link
US (1)	US4250333A (de)
JP (1)	JPS54106438A (de)
AT (1)	AT358559B (de)
BE (1)	BE871395A (de)
BR (1)	BR7806906A (de)
CA (1)	CA1111864A (de)
CH (1)	CH635054A5 (de)
DD (1)	DD140453A5 (de)
DE (1)	DE2845429A1 (de)
DK (1)	DK170156B1 (de)
ES (1)	ES474342A1 (de)
FR (1)	FR2406622A1 (de)
GB (1)	GB2006211B (de)
HU (1)	HU175816B (de)
IE (1)	IE47457B1 (de)
IL (1)	IL55819A (de)
IT (1)	IT1101617B (de)
LU (1)	LU80394A1 (de)
NL (1)	NL190370C (de)
WO (1)	WO1979000219A1 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2932458A1 (de) *	1979-08-10	1981-02-26	Bayer Ag	Herstellung von monoalkylethern von hydroxyphenolen und deren umwandlung zu hydroxycumaranen
DE3018004C2 (de) *	1980-05-10	1982-06-16	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Hydrochinonmonophenyläthern
IT1140948B (it) *	1980-05-16	1986-10-10	Montedison Spa	Processo per la preparazione del mono-metallil-etere della pirocatechina
DE3043230A1 (de) *	1980-11-15	1982-07-08	Bayer Ag, 5090 Leverkusen	Herstellung von monoalkylaethern von hydroxyphenolen
US4465868A (en) *	1981-07-17	1984-08-14	Otsuka Kagaku Yakuhin Kabushiki Kaisha	Process for preparing o-methallyloxyphenol
DE3136810A1 (de) *	1981-09-16	1983-03-31	Bayer Ag, 5090 Leverkusen	Verfahren zur isolierung von dihydroxybenzol-monoethern aus reaktionsgemischen
US4420642A (en) *	1982-02-18	1983-12-13	Fmc Corporation	Selective removal and recovery of catechol mixed with 2-methallyloxyphenol
IT1151718B (it) *	1982-04-19	1986-12-24	Brichima Spa	Procedimento per la preparazione del 2,3-diidro-2,2-dimetilbenzofuran-7-olo
US4639536A (en) *	1984-08-30	1987-01-27	Union Carbide Corporation	Intermediate, its synthesis, and its use in a process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran
DE3439938A1 (de) *	1984-11-02	1986-05-15	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung niedrigmolekularer diglycidylether zweiwertiger phenole
US4618728A (en) *	1985-02-22	1986-10-21	Fmc Corporation	Water aided catechol etherification
US4982012A (en) *	1987-12-18	1991-01-01	Fmc Corporation	Two phase process for preparing 2-methallyloxyphenol from catechol
US4851587A (en) *	1988-05-31	1989-07-25	Fmc Corporation	Single solvent process for preparing 2-methallyloxy-phenol from catechol
RU2203882C1 (ru) *	2001-12-11	2003-05-10	Общество с ограниченной ответственностью "НПК Реактив-Сервис"	Способ получения 1,5-бис(2-гидроксифенокси)-3-оксапентана моногидрата

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3474171A (en) *	1964-01-23	1969-10-21	Fmc Corp	2,2-dimethyl-2,3-dihydrobenzofuranyl-7-n-methylcarbamate
US3927118A (en) *	1973-12-21	1975-12-16	Crown Zellerbach Corp	Process for monoetherification of polyhydric benzenes

1977
- 1977-10-20 FR FR7732340A patent/FR2406622A1/fr active Granted
1978
- 1978-04-19 BR BR7806906A patent/BR7806906A/pt unknown
- 1978-10-12 US US05/951,278 patent/US4250333A/en not_active Expired - Lifetime
- 1978-10-18 NL NLAANVRAGE7810446,A patent/NL190370C/xx not_active IP Right Cessation
- 1978-10-18 GB GB7840983A patent/GB2006211B/en not_active Expired
- 1978-10-18 DE DE19782845429 patent/DE2845429A1/de active Granted
- 1978-10-18 WO PCT/FR1978/000035 patent/WO1979000219A1/fr not_active Ceased
- 1978-10-18 CA CA313,714A patent/CA1111864A/en not_active Expired
- 1978-10-18 IE IE2068/78A patent/IE47457B1/en not_active IP Right Cessation
- 1978-10-19 LU LU80394A patent/LU80394A1/fr unknown
- 1978-10-19 BE BE191229A patent/BE871395A/xx not_active IP Right Cessation
- 1978-10-19 ES ES474342A patent/ES474342A1/es not_active Expired
- 1978-10-19 HU HU78PI644A patent/HU175816B/hu not_active IP Right Cessation
- 1978-10-19 DK DK466878A patent/DK170156B1/da not_active IP Right Cessation
- 1978-10-19 JP JP12902378A patent/JPS54106438A/ja active Granted
- 1978-10-20 CH CH1089478A patent/CH635054A5/fr not_active IP Right Cessation
- 1978-10-20 DD DD78208587A patent/DD140453A5/de not_active IP Right Cessation
- 1978-10-20 IT IT28967/78A patent/IT1101617B/it active
- 1978-10-20 AT AT756178A patent/AT358559B/de not_active IP Right Cessation
- 1978-10-30 IL IL55819A patent/IL55819A/xx unknown

Also Published As

Publication number	Publication date
US4250333A (en)	1981-02-10
DE2845429A1 (de)	1979-04-26
JPS54106438A (en)	1979-08-21
NL190370B (nl)	1993-09-01
FR2406622A1 (fr)	1979-05-18
AT358559B (de)	1980-09-25
HU175816B (hu)	1980-10-28
IE47457B1 (en)	1984-03-21
DD140453A5 (de)	1980-03-05
ATA756178A (de)	1980-02-15
IT1101617B (it)	1985-10-07
IT7828967A0 (it)	1978-10-20
DK170156B1 (da)	1995-06-06
DK466878A (da)	1979-04-21
CA1111864A (en)	1981-11-03
NL190370C (nl)	1994-02-01
IE782068L (en)	1979-04-20
FR2406622B1 (de)	1980-09-05
BR7806906A (pt)	1979-06-26
GB2006211A (en)	1979-05-02
DE2845429C2 (de)	1989-01-05
NL7810446A (nl)	1979-04-24
WO1979000219A1 (fr)	1979-05-03
GB2006211B (en)	1982-02-17
CH635054A5 (fr)	1983-03-15
JPS6339578B2 (de)	1988-08-05
ES474342A1 (es)	1979-04-16
IL55819A (en)	1981-12-31
BE871395A (fr)	1979-04-19

Publication	Publication Date	Title
LU80394A1 (fr)	1980-05-07	Procede de monoetherification selective de la pyrocatechine
CA1249995A (fr)	1989-02-14	Composes a noyau cyclopropanique, procede de preparation et application a la preparation de derives cyclopropaniques a chaine dihalovinylique
EP2760816B1 (de)	2016-08-24	Verfahren zur herstellung von alkoxyphenol und alkoxy-hydroxybenzaldehyd
EP0082049B1 (de)	1987-07-29	Äther mit Chiralenatomen in den organischen Resten, ihre Herstellung, ihre Verwendung in der Spaltung von Alkoholen oder von bestimmten Hemiacetalen und auf diese weise gespaltene Verbindungen
EP0004493B1 (de)	1981-05-06	Äther deren organische Reste asymmetrische Atome enthalten, Verfahren zu ihrer Herstellung und ihre Anwendung zur Spaltung von Alkoholen, Phenolen oder gewissen Verbindungen mit Laktonstruktur
EP0149407B1 (de)	1987-04-01	Verfahren zur Herstellung von Brombenzaldehyden-Hydroxy und/oder Alkoxy substituiert
FR2470768A1 (fr)	1981-06-12	Procede de preparation de derives de benzofuranne
CA2017133C (fr)	1997-01-07	Procede de synthese de cyanures d'acyle
CH654008A5 (fr)	1986-01-31	Procede de preparation de 1,3,7-trialkylxanthines.
EP0001944B1 (de)	1981-11-25	Ester von alpha-halogenierten Alkoholen, Verfahren zur Herstellung und Anwendung bei der Synthese von Estern von alpha-cyano-substituierten Alkoholen
WO1995026326A1 (en)	1995-10-05	Method of purifying fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether
EP0189448B1 (de)	1989-01-25	Fluorierungsmittel für organische verbindungen, insbesondere für acetylenderivate, ihr herstellungsverfahren und ihre verwendung für additions- oder nukleophile substitutionsreaktionen
EP0285500A1 (de)	1988-10-05	Substituierte Harnstoffe, Verfahren zu deren Herstellung und deren Anwendung in der Veredelung zelluloser Fasern
FR2460286A1 (fr)	1981-01-23	Procede de preparation d'acide phenoxy-2 propioniques optiquement actifs
EP0097578B1 (de)	1985-09-11	Verfahren zur Herstellung der 3-Methyl-3-hydroxyglutarsäure und ein Zwischenprodukt zu ihrer Herstellung
FR2589469A1 (fr)	1987-05-07	Procede de preparation de l'acide valproique
CA1111447A (fr)	1981-10-27	Composes halogenes, procede de preparation et application a la preparation du metaphenoxy benzaldehyde
EP0199660B1 (de)	1989-02-08	Verfahren zur Herstellung von aromatischen 1,1-Difluorperhaloalkoxy- oder 1,1-Difluorperhalothioalkylderivaten
CH666677A5 (fr)	1988-08-15	Procede de valorisation sous forme de produits perbromes de produits sous-bromes obtenus en solutions.
FR2491918A1 (fr)	1982-04-16	Procede de preparation de 3-phenoxybenzenes
FR2853901A1 (fr)	2004-10-22	Procede de preparation de derives de l'acide hexahydropyridazine-3-carboxylique
EP0035927B1 (de)	1983-01-26	Verfahren zur Herstellung von Chloralkoxybenzolen
EP0765303A1 (de)	1997-04-02	Verfahren zur herstellung von halogenalkanolen
CH618696A5 (en)	1980-08-15	Process for the preparation of phenoxyacetic acid derivatives
SU1198065A1 (ru)	1985-12-15	Способ получени бензойного эфира @ -изомера 2,5-диметилпиперидола- @