HRP20151390T1 - Postupak za pripremu 2-(2,3-dimetilfenil)-1-propanala - Google Patents

Postupak za pripremu 2-(2,3-dimetilfenil)-1-propanala Download PDF

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Publication number
HRP20151390T1
HRP20151390T1 HRP20151390TT HRP20151390T HRP20151390T1 HR P20151390 T1 HRP20151390 T1 HR P20151390T1 HR P20151390T T HRP20151390T T HR P20151390TT HR P20151390 T HRP20151390 T HR P20151390T HR P20151390 T1 HRP20151390 T1 HR P20151390T1
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reaction
acid
compound
formula
reak
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HRP20151390TT
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Florencio Zaragoza Doerwald
Anna KULESZA
Stephan Elzner
Robert BUJOK
Zbigniew WROBEL
Krzysztof Wojciechowski
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Lonza Ltd
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Priority claimed from PCT/EP2012/070873 external-priority patent/WO2012172120A2/en
Application filed by Lonza Ltd filed Critical Lonza Ltd
Publication of HRP20151390T1 publication Critical patent/HRP20151390T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/86—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • 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
    • C07D233/58—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 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/025—Sulfonic acids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Cosmetics (AREA)

Claims (9)

1. Postupak za pripremu spoja formule (XXI), [image] naznačen time da postupak obuhvaća korak (N); korak (N) obuhvaća reakciju (N-reak.); pri tome se kod reakcije (N-reak.) radi o reakciji spoja formule (XXII) sa katalizatorom (N-kat.); [image] katalizator (N-kat.) je odabran iz skupine koja se sastoji od octene kiseline, mravlje kiseline, trifluoroctene kiseline, metansulfonske kiseline, benzol-sulfonske kiseline, p- toluolsulfonske kiseline, kamfor-sulfonske kiseline, HCl, HBr, H2SO4, HNO3, H3PO4, HClO4, BCl3, BBr3, BF3OEt2, BF3SMe2, BF3THF, MgCl2, MgBr2, MgI2, AlCl3, Al(O-C1-4-alkil)3, SnCl4, TiCl4, Ti (O-C1-4-alkil)4, ZrCl4, Bi2O3, BiCl3, ZnCl2, PbCl2, FeCl3, ScCl3, NiCl2, Yb(OTf)3, Yb(Cl)3, GaCl3, AlBr3, Ce(OTf)3, LiCl, Cu(BF4)2, Cu(OTf)2, NiBr2 (PPh3)2, NiBr2, NiCl2, Pd(OAc)2, PdCl2, PtCl2, InCl3, kiselih anorganskih čvrstih tvari, kiselih smola ionskih izmjenjivača, sa anorganskim kiselinama tretiranog ugljika i njihovih mješavina.
2. Postupak prema zahtjevu 1, naznačen time da je katalizator (N-kat.) odabran iz skupine koja se sastoji od octene kiseline, mravlje kiseline, trifluoroctene kiseline, metansulfonske kiseline, p-toluolsulfonske kiseline, HCl, HBr, H2SO4, H3PO4, BCl3, BF3OEt2, MgCl2, MgBr2, AlCl3, ZnCl2, Cu(BF4)2, aluminosilikata, kiselih smola ionskih izmjenjivača sa HCl, H2SO4 ili HNO3 tretiranim ugljikom i njihovih mješavina.
3. Postupak prema zahtjevu 1 ili 2, naznačen time da se reakcija (N-reak.) provodi u otapalu (N-otop.); otapalo (N-otap.) je izabrano iz skupine koja se sastoji od vode, terc.-butanola, izopropanola, acetonitrila, propionitrila, THF, metil-THF, NMP, dioksana, 1,2-dimetoksietana, diklormetana, 1,2-dikloretana, kloroforma, toluola, benzola, klorbenzola, heksana, cikloheksana, etilnog estera octene kiseline, octene kiseline, mravlje kiseline, trifluoroctene kiseline i njihovih mješavina.
4. Postupak prema jednom ili više zahtjeva 1 do 3, naznačen time da spoj formule (XXII) bude spravljen u jednom koraku (0) ili u dva koraka, a pri tom se u ta dva koraka radi o koracima (O1) i koraku (O2); Korak (O) obuhvaća keakciju (O-reak.); Kod reakcije (O-reak.) radi se o reakciji spoja formule (XXII) sa reagensom (O-reag.); [image] reagens (O-reag.) je odabran iz skupine koja se sastoji od peroctene kiseline, trifluor peroctene kiseline, perbenzoeve kiseline, 3-klorperbenzoeve kiseline, monoperftalatne kiseline, dimetildioksirana, terc.-butilhidroperoksida, dibenzoilperoksida, kumolhidroperoksida, kisika, zraka, natrij hipoklorita, KHSO5, Na2O2, vodenastog H2O2, u octenoj kiselini otopljenog H2O2, u trifluoroctenoj kiselini otopljenog H2O2 i njihovih mješavina; Korak (O1) obuhvaća reakciju (O1-reak.); Kod reakcije (O1-reak.) se radi o reakciji (O1-reak.) spoja formule (XXII) sa vodom i jednim spojem (O1-spoj); Spoj (O1-spoj) je odabran iz skupine broma, N-bromsukcinimida, klora, N-klorsukcinimida, joda, N-jodsukcinimida, IBr, BrCl i njihovih mješavina; Korak (O2) obuhvaća reakciju (O2-reak.); Kod reakcije (O2-reak.) se radi o reakciji reakcijskog produkta reakcije (O1-reak.) s jednom bazom (O2-baza); Baza (O2-baza) je iz skupine koja se sastoji od natrij-hidroksida, kalij-hidroksida, kalcij-hidroksida i njihovih mješavina.
5. Postupak prema zahtjevu 4, naznačen time da reagens (0-reag.) je iz skupine, koja se sastoji od peroctene kiseline, terc.-butilhidroperoksida, kisika, zraka, natrij hipoklorita, vodenastog H2O2, u octenoj kiselini otopljenog H2O2, u trifluoroctenoj kiselini otopljenom H2O2 i njihovih mješavina.
6. Postupak prema zahtjevu 4 ili 5, naznačen time da spoj formule (XXIII) bude spravljen u jednom koraku; Korak (P) obuhvaća reakciju (P-reak.); Kod reakcije (P-reak.) spoj (XXIV) bude podvrgnut temperaturi (P-temp.); [image] temperatura (P-temp.) iznosi 0 do 300°C.
7. Postupak prema zahtjevu 6, naznačen time da spoj formule (XXIV) bude spravljen u tri koraka, pri čemu se radi o tri koraka, korak (Q1), korak (Q2) i korak (Q3); Korak (Q1) je reakcija (Q1-reak.) koja obuhvaća reakciju formule (XXV) sa jednim reagensom (Q1-reag); [image] Q stoji za Br, Cl ili I; Reagens (Q1-reag.) je odabran iz skupine koja se sastoji iz litija, magnezija, aluminija, cinka, kalcija, izopropilmagnezijklorida, izopropilmagnezijbromida, butillitija, sec.-butillitija i njihovih mješavina; Korak (Q2) obuhvaća reakciju (Q2-reak.); Kod reakcije (Q2-reak.) se radi o reakciji reakcijskog produkta rekacije (Q1-reak.) sa acetonom; Korak (Q3) obuhvaća reakciju Q3; Kod reakcije (Q3-reak.) se radi o reakciji reakcijskog produkta reakcije (Q2-reak.) sa jednim reagensom (Q3-reag.); Reagens (Q3-reag.) je odabran iz skupine koja se sastoji iz vode, metanola, etanola, oksalne kiseline, limunske kiseline, NH4Cl, HCl, HBr, HNO3, H2SO4, H3PO4, octene kiseline, propionske kiseline, mravlje kiseline i njihovih mješavina.
8. Primjena spoja formule (XXI) kao mirisne tvari, naznačen time da je spoj formule (XXI) definiran kao u zahtjevu 1.
9. Primjena spoja formule (XXI) za spravljanje medetomidina, naznačen time da je spoj formule (XXI) definiran kao u zahtjevu 1.
HRP20151390TT 2012-05-08 2015-12-18 Postupak za pripremu 2-(2,3-dimetilfenil)-1-propanala HRP20151390T1 (hr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201261644198P 2012-05-08 2012-05-08
EP12167135 2012-05-08
EP12187354 2012-10-05
PCT/EP2012/070873 WO2012172120A2 (en) 2012-05-08 2012-10-22 2-(2,3-dimethylphenyl)-1-propanal and its use as perfume
EP12192621 2012-11-14
EP12784297.9A EP2847157B1 (en) 2012-05-08 2012-11-15 Method for preparation of 2-(2,3-dimethylphenyl)-1-propanal
PCT/EP2012/072797 WO2013011156A2 (en) 2012-05-08 2012-11-15 Method for preparation of 2-(2,3-dimethylphenyl)-1-propanal

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HRP20151390T1 true HRP20151390T1 (hr) 2016-01-15

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US (1) US9126915B2 (hr)
EP (1) EP2847157B1 (hr)
JP (1) JP5777840B2 (hr)
KR (1) KR101537204B1 (hr)
CN (1) CN104203893B (hr)
AU (1) AU2012285676B2 (hr)
CA (1) CA2866431C (hr)
CL (2) CL2014002908A1 (hr)
CY (1) CY1117404T1 (hr)
DK (1) DK2847157T3 (hr)
EA (2) EA029130B1 (hr)
ES (1) ES2557638T3 (hr)
HK (1) HK1201060A1 (hr)
HR (1) HRP20151390T1 (hr)
HU (1) HUE026686T2 (hr)
IN (1) IN2014DN07982A (hr)
MY (1) MY165212A (hr)
PL (1) PL2847157T3 (hr)
PT (1) PT2847157E (hr)
SG (1) SG11201405611SA (hr)
TW (1) TWI531557B (hr)
WO (1) WO2013011156A2 (hr)

Families Citing this family (6)

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Publication number Priority date Publication date Assignee Title
IN2014DN07983A (hr) * 2012-05-08 2015-05-01 Lonza Ag
EA029130B1 (ru) * 2012-05-08 2018-02-28 Лонца Лтд Применение соединения для получения медетомидина
WO2013011157A1 (en) 2012-06-28 2013-01-24 Lonza Ltd Method for preparation of medetomidine with chloroacetone
DK2867195T3 (en) 2012-06-28 2016-04-04 Lonza Ag PROCESS FOR THE PREPARATION OF 2- (2,3-dimethylphenyl) -1-propanal WITH chloroacetone
WO2016074118A1 (en) * 2014-11-10 2016-05-19 Givaudan Sa Improvements in or relating to organic compounds
JP7464211B2 (ja) * 2020-12-21 2024-04-09 エルジー・ケム・リミテッド α－メチルスチレンの製造方法

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DK2867195T3 (en) * 2012-06-28 2016-04-04 Lonza Ag PROCESS FOR THE PREPARATION OF 2- (2,3-dimethylphenyl) -1-propanal WITH chloroacetone
WO2012172121A1 (en) * 2012-06-28 2012-12-20 Lonza Ltd Method for the preparation of medetomidine with chloroacetone
WO2013011157A1 (en) * 2012-06-28 2013-01-24 Lonza Ltd Method for preparation of medetomidine with chloroacetone
WO2012172122A2 (en) * 2012-06-28 2012-12-20 Lonza Ltd Method for the preparation of 2-(2,3-dimethylphenyl)-1-propanal

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PL2847157T3 (pl) 2016-04-29
JP5777840B2 (ja) 2015-09-09
CL2016001663A1 (es) 2017-01-06
DK2847157T3 (en) 2016-02-08
NZ700641A (en) 2016-02-26
CA2866431C (en) 2017-06-27
TW201412697A (zh) 2014-04-01
US20150080287A1 (en) 2015-03-19
PT2847157E (pt) 2016-01-27
CN104203893A (zh) 2014-12-10
WO2013011156A2 (en) 2013-01-24
EP2847157B1 (en) 2015-10-28
MY165212A (en) 2018-03-05
AU2012285676B2 (en) 2016-02-25
EP2847157A2 (en) 2015-03-18
EA025591B1 (ru) 2017-01-30
WO2013011156A3 (en) 2013-04-04
HUE026686T2 (en) 2016-07-28
CA2866431A1 (en) 2013-01-24
SG11201405611SA (en) 2014-11-27
CL2014002908A1 (es) 2014-12-19
CN104203893B (zh) 2016-02-03
KR20140139076A (ko) 2014-12-04
HK1201060A1 (zh) 2015-08-21
EA201400937A1 (ru) 2015-01-30
IN2014DN07982A (hr) 2015-05-01
JP2015517473A (ja) 2015-06-22
EA029130B1 (ru) 2018-02-28
TWI531557B (zh) 2016-05-01
EA201691508A1 (ru) 2016-11-30
CY1117404T1 (el) 2017-04-26
KR101537204B1 (ko) 2015-07-22
US9126915B2 (en) 2015-09-08

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