CH620914A5 - Process for preparing 2,5-dimethyl-3(2H)-furanone - Google Patents

Process for preparing 2,5-dimethyl-3(2H)-furanone Download PDF

Info

Publication number: CH620914A5
Authority: CH; Switzerland
Prior art keywords: acid; formula; dimethyl; solution; furanone
Prior art date: 1974-02-15

Application number

CH179575A

Other languages

English (en)

Italian (it)

Inventor

Carlo Venturello

Rino D Aloisio

Original Assignee

Montedison Spa

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.)

1974-02-15

Filing date

1975-02-13

Publication date

1980-12-31

1975-02-13 Application filed by Montedison Spa filed Critical Montedison Spa

1980-12-31 Publication of CH620914A5 publication Critical patent/CH620914A5/it

Links

HVNICCSXGONRCB-UHFFFAOYSA-N 2,2-dimethylfuran-3-one Chemical compound CC1(C)OC=CC1=O HVNICCSXGONRCB-UHFFFAOYSA-N 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 20
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 7
239000011347 resin Substances 0.000 claims abstract description 6
229920005989 resin Polymers 0.000 claims abstract description 6
125000002091 cationic group Chemical group 0.000 claims abstract description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 5
239000011707 mineral Substances 0.000 claims abstract description 5
238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 4
238000005882 aldol condensation reaction Methods 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract 4
150000007524 organic acids Chemical class 0.000 claims abstract 3
239000000987 azo dye Substances 0.000 claims abstract 2
238000003786 synthesis reaction Methods 0.000 claims abstract 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
239000000539 dimer Substances 0.000 claims description 11
230000009466 transformation Effects 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
230000007062 hydrolysis Effects 0.000 claims description 8
238000006460 hydrolysis reaction Methods 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
229960000583 acetic acid Drugs 0.000 claims 1
239000003377 acid catalyst Substances 0.000 claims 1
150000001540 azides Chemical class 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
239000003729 cation exchange resin Substances 0.000 claims 1
DNYLSCDHFCSDRM-UHFFFAOYSA-N ethyl 2,5-dimethylfuran-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C)OC=1C DNYLSCDHFCSDRM-UHFFFAOYSA-N 0.000 claims 1
JGRPZAGOYKNIAC-UHFFFAOYSA-N ethyl n-propan-2-ylcarbamate Chemical compound CCOC(=O)NC(C)C JGRPZAGOYKNIAC-UHFFFAOYSA-N 0.000 claims 1
YKSPDHDZLUZVDJ-UHFFFAOYSA-N furan-2-carbonyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CC=CO1 YKSPDHDZLUZVDJ-UHFFFAOYSA-N 0.000 claims 1
239000012362 glacial acetic acid Substances 0.000 claims 1
229940093915 gynecological organic acid Drugs 0.000 claims 1
235000005985 organic acids Nutrition 0.000 claims 1
230000035484 reaction time Effects 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
239000000243 solution Substances 0.000 abstract description 23
239000000047 product Substances 0.000 abstract description 19
TUYBNEBXRHKEKQ-UHFFFAOYSA-N 5-acetyl-2-hydroxy-2,5-dimethyloxolan-3-one Chemical compound CC(=O)C1(C)CC(=O)C(C)(O)O1 TUYBNEBXRHKEKQ-UHFFFAOYSA-N 0.000 abstract description 5
239000002904 solvent Substances 0.000 abstract description 5
239000007864 aqueous solution Substances 0.000 abstract description 4
238000004043 dyeing Methods 0.000 abstract description 4
239000007795 chemical reaction product Substances 0.000 abstract description 2
239000000976 ink Substances 0.000 abstract description 2
239000000463 material Substances 0.000 abstract description 2
239000003973 paint Substances 0.000 abstract description 2
239000004033 plastic Substances 0.000 abstract description 2
229920003023 plastic Polymers 0.000 abstract description 2
229920002994 synthetic fiber Polymers 0.000 abstract description 2
239000004758 synthetic textile Substances 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000003756 stirring Methods 0.000 description 11
ASOSVCXGWPDUGN-UHFFFAOYSA-N 2,5-Dimethyl-3(2H)-furanone Chemical compound CC1OC(C)=CC1=O ASOSVCXGWPDUGN-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
FORCWSNQDMPPOC-UHFFFAOYSA-N 5-methyl-4-(3-methyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)-2-phenyl-4h-pyrazol-3-one Chemical compound CC1=NN(C=2C=CC=CC=2)C(=O)C1C(C1=O)C(C)=NN1C1=CC=CC=C1 FORCWSNQDMPPOC-UHFFFAOYSA-N 0.000 description 7
238000004821 distillation Methods 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000012670 alkaline solution Substances 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
239000000049 pigment Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000012954 diazonium Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 3
230000027326 copulation Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
-1 NaCl Chemical class 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical class NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical class NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
WGVHNCAJPFIFCR-UHFFFAOYSA-N 5-methyl-1,2-dihydropyrazol-3-one Chemical compound CC1=CC(O)=NN1 WGVHNCAJPFIFCR-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241001579016 Nanoa Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241001342522 Vampyrum spectrum Species 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
RUKCJUBTRDGPCC-UHFFFAOYSA-N acetic acid;acetyl acetate Chemical compound CC(O)=O.CC(=O)OC(C)=O RUKCJUBTRDGPCC-UHFFFAOYSA-N 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000002826 coolant Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide

Landscapes

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

CH179575A 1974-02-15 1975-02-13 Process for preparing 2,5-dimethyl-3(2H)-furanone CH620914A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT41004/74A IT1005472B (it)	1974-02-15	1974-02-15	Procedimento per la preparazione del 2,5, dimetil 3,2h, furanone

Publications (1)

Publication Number	Publication Date
CH620914A5 true CH620914A5 (en)	1980-12-31

Family

ID=11250022

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH179575A CH620914A5 (en)	1974-02-15	1975-02-13	Process for preparing 2,5-dimethyl-3(2H)-furanone

Country Status (11)

Country	Link
US (1)	US3980675A (de)
JP (1)	JPS5920671B2 (de)
BE (1)	BE825575A (de)
CA (1)	CA1055510A (de)
CH (1)	CH620914A5 (de)
DE (1)	DE2505902C2 (de)
ES (1)	ES434712A1 (de)
FR (1)	FR2261279B1 (de)
GB (1)	GB1496411A (de)
IT (1)	IT1005472B (de)
NL (1)	NL7501651A (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4234616A (en) *	1979-08-03	1980-11-18	International Flavors & Fragrances Inc.	Flavoring with mixtures of 2,5-dialkyl dihydrofuranones and 2,4,5-trialkyl dihydrofuranones
JPS60146379U (ja) *	1984-03-07	1985-09-28	株式会社東芝	チツプ部品塔載用印刷配線板
GB8714005D0 (en) *	1987-06-16	1987-07-22	Sandoz Ltd	Organic compounds
US5698585A (en)	1995-04-13	1997-12-16	Kikkoman Corporation	Pharmaceutical preparation for prevention and/or treatment for cataract
WO2007141102A1 (en) *	2006-06-02	2007-12-13	Symrise Gmbh & Co. Kg	Use of diacetyl dimer as an aromatic and/or flavouring substance
EP2112139A1 (de) *	2008-04-25	2009-10-28	Laboratorios Del. Dr. Esteve, S.A.	Verfahren zur Herstellung von bei der Synthese von Sigma-Rezeptorinhibitoren nützlichen Naphthalen-2-yl-pyrazol-3-on-Zwischenprodukten
EP2116539A1 (de)	2008-04-25	2009-11-11	Laboratorios Del. Dr. Esteve, S.A.	1-Aryl-3-Amino-alkoxy-pyrazole als Sigma-Liganden zur Verbesserung der analgetischen Wirkung von Opioiden und zur Schwächung der Abhängigkeit davon
EP2353598A1 (de)	2010-02-04	2011-08-10	Laboratorios Del. Dr. Esteve, S.A.	Sigma-Liganden zur Anwendung in der Vorbeugung und/oder Behandlung von postoperativem Schmerz
EP2353591A1 (de)	2010-02-04	2011-08-10	Laboratorios Del. Dr. Esteve, S.A.	Sigma-Liganden zur Verstärkung der analgesischen Wirkung von Opioden und Opiaten bei postoperativem Schmerz und zur Schwächung der Abhängigkeit davon
EP2388005A1 (de)	2010-05-21	2011-11-23	Laboratorios Del. Dr. Esteve, S.A.	Sigma-Liganden zur Vorbeugung und/oder Behandlung von Erbrechen infolge von Chemotherapie oder Strahlentherapie
EP2415471A1 (de)	2010-08-03	2012-02-08	Laboratorios Del. Dr. Esteve, S.A.	Verwendung von Sigmaliganden bei opioidinduzierter Hyperalgesie
EP2524694A1 (de)	2011-05-19	2012-11-21	Laboratorios Del. Dr. Esteve, S.A.	Verwendung von Sigmaliganden bei Schmerz im Zusammenhang mit Typ-2-Diabetes
SG11201604480PA (en)	2013-12-17	2016-07-28	Esteve Labor Dr	SEROTONIN-NOREPINEPHRINE REUPTAKE INHIBITORS (SNRIs) AND SIGMA RECEPTOR LIGANDS COMBINATIONS

1974
- 1974-02-15 IT IT41004/74A patent/IT1005472B/it active
1975
- 1975-02-12 NL NL7501651A patent/NL7501651A/xx not_active Application Discontinuation
- 1975-02-13 CH CH179575A patent/CH620914A5/it not_active IP Right Cessation
- 1975-02-13 DE DE2505902A patent/DE2505902C2/de not_active Expired
- 1975-02-13 JP JP50017550A patent/JPS5920671B2/ja not_active Expired
- 1975-02-14 US US05/550,137 patent/US3980675A/en not_active Expired - Lifetime
- 1975-02-14 BE BE153400A patent/BE825575A/xx not_active IP Right Cessation
- 1975-02-14 GB GB6401/75A patent/GB1496411A/en not_active Expired
- 1975-02-14 ES ES434712A patent/ES434712A1/es not_active Expired
- 1975-02-14 FR FR7504614A patent/FR2261279B1/fr not_active Expired
- 1975-02-17 CA CA220,297A patent/CA1055510A/en not_active Expired

Also Published As

Publication number	Publication date
US3980675A (en)	1976-09-14
IT1005472B (it)	1976-08-20
DE2505902A1 (de)	1975-08-21
GB1496411A (en)	1977-12-30
DE2505902C2 (de)	1983-11-10
FR2261279B1 (de)	1977-04-15
FR2261279A1 (de)	1975-09-12
NL7501651A (nl)	1975-08-19
JPS5920671B2 (ja)	1984-05-15
ES434712A1 (es)	1977-02-01
JPS50123659A (de)	1975-09-29
CA1055510A (en)	1979-05-29
BE825575A (fr)	1975-08-14

Legal Events

Date	Code	Title	Description
1992-10-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US3980675A (en)	1976-09-14	Process for preparing 2,5-dimethyl-3-(2H)-furanone
DE2805488C2 (de)	1985-06-27	Tetrahydrofuran-Solvate der Magnesiumhalogenid-Komplexe der &alpha;-Brompropionsäure, Verfahren zu deren Herstellung und deren Weiterverarbeitung zur Herstellung von 2-Arylpropionsäuren
DE3212170C2 (de)	1989-03-02
DE2819886C2 (de)	1988-03-31
DE69608862T2 (de)	2001-02-22	Verfahren zur Herstellung einer optisch aktiven 2-Hydroxy-4-Arylbuttersäure oder deren Ester und Zwischenprodukt dafür
CH637618A5 (de)	1983-08-15	Verfahren zur herstellung von anthrachinon.
DE3314029C2 (de)	1993-03-04
DE3033003C2 (de)	1987-03-12	Verfahren zur Herstellung von gegebenenfalls kernsubstituierten N-(3-Aminophenyl-)glykolsäureamiden
US3717673A (en)	1973-02-20	Process for the preparation of l-dopa
US3803177A (en)	1974-04-09	Process for production of eriodictyol
DE2015760A1 (de)	1971-03-25	Verfahren zur Herstellung von Glucofuranosiden
DE1645918C3 (de)	1973-10-04	Verfahren zur Herstellung des Salicyl saureesters des beta Pyridyl carbinols
DE1493619C (de)	1973-01-25	Verfahren zur Herstellung von 3-(3,4-Dihydroxyphenyl)-2-methylalanin
SHIRLEY et al.	1957	Structure and Reactions of Gossypol. V. Methylapogossypol Hexamethyl Ether and 2, 3-Dimethoxy-4-isopropyl-5-allyltoluene1, 2
RU2069656C1 (ru)	1996-11-27	Способ получения 4-нитро-1,3-диаминобензола
AT368165B (de)	1982-09-27	Verfahren zur herstellung von neuen magnesiumverbindungen
AT367063B (de)	1982-05-25	Verfahren zur herstellung einer neuen magnesiumverbindung
KR850001036B1 (ko)	1985-07-19	2-아미노-4-메틸피리딘의 아미드의 제조방법
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