DK155594B - 3,3-dimethyl-1-phenoxybutan-2-oler - Google Patents
3,3-dimethyl-1-phenoxybutan-2-oler Download PDFInfo
- Publication number
- DK155594B DK155594B DK098781AA DK98781A DK155594B DK 155594 B DK155594 B DK 155594B DK 098781A A DK098781A A DK 098781AA DK 98781 A DK98781 A DK 98781A DK 155594 B DK155594 B DK 155594B
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- dimethyl
- ols
- growth
- phenoxybutan
- Prior art date
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- PWCKSOLBQNLCRR-UHFFFAOYSA-N 3,3-dimethyl-1-phenoxybutan-2-ol Chemical class CC(C)(C)C(O)COC1=CC=CC=C1 PWCKSOLBQNLCRR-UHFFFAOYSA-N 0.000 title claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000012010 growth Effects 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- HEAYDCIZOFDHRM-UHFFFAOYSA-N 2-tert-butyloxirane Chemical compound CC(C)(C)C1CO1 HEAYDCIZOFDHRM-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- JJHMFMLNPPNLAL-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethylbutan-2-ol Chemical compound CC(C)(C)C(O)COC1=CC=C(Cl)C=C1 JJHMFMLNPPNLAL-UHFFFAOYSA-N 0.000 description 2
- IHJOPKUEXSZUNC-UHFFFAOYSA-N 3,3-dimethyl-1-phenoxy-1-(1h-pyrrol-2-yl)butan-2-one Chemical class C=1C=CNC=1C(C(=O)C(C)(C)C)OC1=CC=CC=C1 IHJOPKUEXSZUNC-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CGLXGSYPQYDTDY-UHFFFAOYSA-N 3,3-dimethyl-1-phenoxybutan-2-one Chemical class CC(C)(C)C(=O)COC1=CC=CC=C1 CGLXGSYPQYDTDY-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 235000021537 Beetroot Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- -1 benzene and toluene Chemical compound 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
Description
DK 155594B
i
Den foreliggende opfindelse angår hidtil ukendte 3,3-dimethyl-l-phenoxybutan-2-oler, som er ejendommelige ved, at de har den almene formel
OH
- 0 - CH2 - CH - C(CH3)3 (I) „ . Tn hvori Y betyder chlor eller phenyl, og 10 n betyder 0 eller 1, der udviser gode plantevækstregulerende egenskaber.
3,3-Dimethyl-l-phenoxybutan-2-olerne med formlen (I) fås, når tert.butyloxiran med formlen 15 CH2 —· HC - C(CH3)3 (II) 20 omsættes med phenoler med formlen (HI) n 25 hvori Y og n har de tidligere angivne betydninger, i nærværelse af et fortyndingsmiddel og i nærværelse af en base.
Anvendes der eksempelvis tert.butyloxiran og 4-chlor-30 phenol som udgangsforbindelser, kan reaktionsforløbet illustreres ved det følgende reaktionsskemai C&— CH - C(CH3 )3 ^ \ / + Cl-(()>-0H -> 35 ° y C1_<0"°*CH2-®_C(CH!)s 2
DK 155594 B
Den ved omsætningen anvendte tert.butyloxiran med formlen (IX) er kendt, jfr. f.eks. J.Chem. Soc. 1963. 1321.
De derudover som udgangsforbindelser anvendte phenoler er alment definerede ved formlen (III).
5 Phenolerne med formlen (III) er alment kendte for bindelser fra den organiske kemi.
Omsætningen gennemføres som nævnt i nærværelse af en base. Som sådanne kan alle gængse organiske og uorganiske baser anvendes. Hertil hører eksempelvis aminer, såsom tri-10 ethylamin, alkalimetalhydroxider, såsom natrium- og kaliumhydroxid, eller alkoholater, såsom natrium- og kaliummethylat eller -ethylat.
Som fortyndingsmidler kommer vand og/eller organiske opløsningsmidler på tale. Der skal eksempelvis nævnes keto-15 ner, såsom acetone og methylisobutylketon, alkoholer, såsom methanol og ethanol, ethere, såsom diisopropylether, tetra-hydrofuran og dioxan, aromatiske carbonhydrider, såsom benzen og toluen, og formamider, såsom dimethylformamid.
Reaktionstemperaturerne kan ved omsætningen varieres 20 i et større område. I almindelighed arbejdes der mellem 0 og 150°C, fortrinsvis mellem 20 og 100°C.
Ved gennemførelsen af omsætningen anvendes der til 1 mol tert.butyloxiran med formlen (II) fortrinsvis 1 til 2 mol, især 1 til 1,5 mol phenol med formlen (III) . Isoleringen 25 af slutprodukterne med formlen (I) sker på almindelig gængs måde.
Foruden at være anvendelige som plantevækstregulerende midler er de hidtil ukendte 3,3-dimethyl-l-phenoxybutan-2-oler med formlen (I) i øvrigt anvendelige som mellemproduk-30 ter. De omdannes let til 3,3-dimethyl-l-phenoxybutan-2-oner med formlen uT)\ - 0 - CH2 - CO - C(CH3) 3 (IV) 35 γ'*—' n 3
DK 155594 B
hvori Y og n har de tidligere angivne betydninger, ved, at forbindelserne med formlen (I) oxideres på gængs måde, f.eks. med luftens oxygen, kaliumpermanganat, brunsten, chlor eller kaliumdichromat, eller ved, at forbindelserne 5 med formlen (I) dehydreres på gængs måde, f.eks. med ædelmetalkatalysatorer, kobberchromit eller nitrobenzen.
Forbindelserne med formlen (IV) kan ved yderligere halogenering, fortrinsvis med sulfurylchlorid eller med brom, på almindelig gængs måde omdannes til de tilsvarende 10 1-chlor(brom)-3,3-dimethyl-l-phenoxybutan-2-oner, jfr. også DE-A1 nr. 2 401 715, der let kan omsættes med 1,2,4-triazol eller imidazol eller imidazol til l-azolyl-3,3-dimethyl-l-phenoxybutan-2-onerne med formlen 15 “ 0 " CH " C° " c(ch3) 3 (V)
Tn hvori Y og n har de tidligere angivne betydninger, og 20 Az betyder 1,2,4-triazol-l-yl, 1,2,4-triazol-4-yl eller imidazol-l-yl, jfr. også DE-A1 nr. 2 401 715.
l-Azolyl-3,3-dimethyl-l-phenoxybutan-2-onerne med formlen (V) udviser stærke fungicide egenskaber, jfr. DE-B2 nr. 2 201 063 og DE-Al nr. 2 325 156.
25 De hidtil ukendte 3,3-dimethyl-l-phenoxybutan-2-oler udviser som nævnt en vækstregulerende virkning.
Det følgende sammenligningsforsøg viser f.eks. virkningen af l-(4-chlorphenoxy)-3,3-dimethylbutan-2-ol ved sukkerroer i forhold til de ubehandlede kontroller.
30 Vækstindflvdelse ved sukkerroer Opløsningsmiddel: 30 vægtdele dimethylformamid Emulgator: 1 vægtdel polyoxyethylen-sorbitan- monolaurat 35 Til fremstilling af et hensigtsmæssigt præparat af virksom forbindelse blandes 1 vægtdel virksom forbindelse med de angivne mængder opløsningsmiddel og emulgator, og 4
DK 155594 B
der fyldes op med vand til den ønskede koncentration.
Sukkerroer dyrkes i væksthus indtil fuld udvikling af kimbladene. I dette stadium sprøjtes planterne drivvåde med præparatet af virksom forbindelse. Efter 14 dage måles 5 planternes tilvækst, og vækstindflydelsen beregnes i procent af tilvæksten af kontrolplanterne. Herved betyder 0%'s vækst-indflydelse en vækst, der svarer til kontrolplanternes. Negative værdier udtrykker en væksthæmning, positive værdier en vækstfremning i forhold til kontrolplanterne.
10
Tabel Vækstindflydelse ved sukkerroer
Koncentration Vækstindflydelse
Virksom forbindelse i ppm i % 15 -
Kontrol - -0
OH
Cl-O^O-CHa-CH-CiCHs )3 500 +15* 20 * særligt tykke blade.
Fremstillinaseksempel
OH
cl-@ - O - CH2 - CH - C(CH3,3
Til 12,8 g (0,1 mol) 4-chlorphenol og 4 g natriumhydroxid i 20 ml vand sættes der 5 g (0,05 mol) tert.butyl-30 oxiran. Reaktionsblandingen omrøres i 24 timer ved 60°C, og derpå fortyndes der med ca. 100 ml vand. Der ekstraheres tre gange med hver gang 50 ml methylenchlorid. De samlede organiske faser vaskes med henblik på fjernelse af ikke omsat phenol med fortyndet vandig natriumhydroxid, tørres 35 over natriumsulfat og inddampes. Remanensen destilleres i vakuum. Der fås 5,9 g, svarende til 52% af det teoretiske udbytte, l-(4-chlorphenoxy)-3,3-dimethylbutan-2-ol med kogepunkt 105eC/0,5 mm Hg.
Claims (1)
- DK 155594B Patentkrav . 3,3-dimethyl-l-phenoxybutan-2-oler, kendetegnet ved, at de har den almene formel /0\ -0-CH2 -CB-C (CH3) 3 (i) Y ^ n hvori 10. betyder chlor eller phenyl, og n betyder 0 eller 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803008477 DE3008477A1 (de) | 1980-03-05 | 1980-03-05 | 3,3-dimethyl-1-phenoxy-butan-2-ole, verfahren zu ihrer herstellung sowie ihre verwendung als zwischenprodukte |
| DE3008477 | 1980-03-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK98781A DK98781A (da) | 1981-09-06 |
| DK155594B true DK155594B (da) | 1989-04-24 |
| DK155594C DK155594C (da) | 1989-09-11 |
Family
ID=6096367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK098781A DK155594C (da) | 1980-03-05 | 1981-03-04 | 3,3-dimethyl-1-phenoxybutan-2-oler |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4339612A (da) |
| EP (1) | EP0035697B1 (da) |
| JP (1) | JPS56139435A (da) |
| BR (1) | BR8101238A (da) |
| CA (1) | CA1161442A (da) |
| DE (2) | DE3008477A1 (da) |
| DK (1) | DK155594C (da) |
| HU (1) | HU187770B (da) |
| IL (1) | IL62276A (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4654162A (en) * | 1984-08-13 | 1987-03-31 | Chisso Corporation | Alcohol derivatives |
| US4618727A (en) * | 1984-11-05 | 1986-10-21 | The Dow Chemical Company | Nitro substituted diphenyl ethers |
| US4973764A (en) * | 1986-10-24 | 1990-11-27 | Exxon Research And Engineering Company | Alkylphenols and derivatives thereof via phenol alkylation by cracked petroleum distillates |
| FI95567C (fi) * | 1987-12-25 | 1996-02-26 | Daiichi Seiyaku Co | Propoksibentseenijohdannaisia ja menetelmä niiden valmistamiseksi |
| DE3800306A1 (de) * | 1988-01-08 | 1989-07-20 | Basf Ag | Tert.-butylalkinole, verfahren zu ihrer herstellung und deren verwendung |
| JP2830151B2 (ja) * | 1989-09-01 | 1998-12-02 | 住友化学工業株式会社 | 光学活性なアルカノール類の製造法 |
| JP2890000B2 (ja) * | 1991-10-11 | 1999-05-10 | 花王株式会社 | １−（２，６−ジメチルフェニルオキシ）−２−アルカノール及びこれを含有する香料組成物 |
| CN102584551B (zh) * | 2012-02-03 | 2014-12-17 | 盐城利民农化有限公司 | 一种***酮中间体1-(4-氯代苯氧基）-1-氯代频哪酮的合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2916520A (en) * | 1959-12-08 | Production of glycol monoethers | ||
| DE1593857A1 (de) * | 1967-02-28 | 1970-10-29 | Bayer Ag | Verfahren zur Herstellung von Mono-Glykolaethern |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912752A (en) * | 1972-01-11 | 1975-10-14 | Bayer Ag | 1-Substituted-1,2,4-triazoles |
| DE2713777C3 (de) * | 1977-03-29 | 1979-10-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von l-Azolyl-33-dimethyl-l-phenoxy-butan-2-onen |
-
1980
- 1980-03-05 DE DE19803008477 patent/DE3008477A1/de not_active Withdrawn
-
1981
- 1981-02-13 US US06/234,529 patent/US4339612A/en not_active Expired - Fee Related
- 1981-02-25 EP EP81101349A patent/EP0035697B1/de not_active Expired
- 1981-02-25 DE DE8181101349T patent/DE3160009D1/de not_active Expired
- 1981-02-27 BR BR8101238A patent/BR8101238A/pt unknown
- 1981-03-02 JP JP2851781A patent/JPS56139435A/ja active Granted
- 1981-03-03 HU HU81521A patent/HU187770B/hu not_active IP Right Cessation
- 1981-03-03 IL IL62276A patent/IL62276A/xx unknown
- 1981-03-04 CA CA000372285A patent/CA1161442A/en not_active Expired
- 1981-03-04 DK DK098781A patent/DK155594C/da not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2916520A (en) * | 1959-12-08 | Production of glycol monoethers | ||
| DE1593857A1 (de) * | 1967-02-28 | 1970-10-29 | Bayer Ag | Verfahren zur Herstellung von Mono-Glykolaethern |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0131492B2 (da) | 1989-06-26 |
| BR8101238A (pt) | 1981-09-08 |
| DE3008477A1 (de) | 1981-09-17 |
| DE3160009D1 (en) | 1983-01-20 |
| US4339612A (en) | 1982-07-13 |
| EP0035697B1 (de) | 1982-12-15 |
| JPS56139435A (en) | 1981-10-30 |
| IL62276A (en) | 1984-05-31 |
| IL62276A0 (en) | 1981-05-20 |
| CA1161442A (en) | 1984-01-31 |
| DK155594C (da) | 1989-09-11 |
| EP0035697A1 (de) | 1981-09-16 |
| HU187770B (en) | 1986-02-28 |
| DK98781A (da) | 1981-09-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |