DK2847157T3 - Fremgangsmåde til fremstilling af 2-(2,3-dimethylphenyl)-1-propanal - Google Patents

Fremgangsmåde til fremstilling af 2-(2,3-dimethylphenyl)-1-propanal Download PDF

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DK2847157T3
DK2847157T3 DK12784297.9T DK12784297T DK2847157T3 DK 2847157 T3 DK2847157 T3 DK 2847157T3 DK 12784297 T DK12784297 T DK 12784297T DK 2847157 T3 DK2847157 T3 DK 2847157T3
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reaction
acid
reac
compound
formula
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Doerwald Florencio Zaragoza
Anna Kulesza
Stephan Elzner
Robert Bujok
Zbigniew Wrobel
Krzysztof Wojciechowski
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Lonza Ag
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Priority claimed from PCT/EP2012/070873 external-priority patent/WO2012172120A2/en
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    • 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
    • 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
    • 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
    • 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)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (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. FREMGANGSMÅDE TIL FREMSTILLING AF 2-(2,3-DIMETHYLPHENYL)-1- PROPANAL
    1. Fremgangsmåde til fremstilling af en forbindelse med formlen (XXI),
    (XXI) fremgangsmåden omfatter et trin (N); trin (N) omfatter en reaktion (N-reac); reaktion (N-reac) er en reaktion af forbindelsen med formlen (XXII) med en katalysator (N-cat);
    (XXII) katalysator (N-cat) er udvalgt fra gruppen bestående af eddikesyre, myresyre, trifluoreddikesyre, methansulfonsyre, benzensulfonsyre, p-toluensulfonsyre, camphorsulfonsyre, HCI, HBr, H2S04, HN03, H3P04, HCI04, BCI3, BBr3, BF3OEt2, BF3SMe2, BF3THF, MgCI2, MgBr2, Mgl2, AICI3, AI(0-Ci_4-alkyl)3, SnCI4, TiCI4, Ti(0-Ci.4-alkyl)4, ZrCI4, Bi203, BiCI3, ZnCI2, PbCI2, FeCI3, ScCI3, NiCI2, Yb(OTf)3, Yb(CI)3, GaCI3, AIBr3, Ce(OTf)3, LiCI, Cu(BF4)2, Cu(OTf)2, NiBr2(PPh3)2, NiBr2, NiCI2, Pd(OAc)2, PdCI2, PtCI2, lnCI3, surt uorganisk faststof, sur ionbytterharpiks, carbon behandlet med uorganisk syre og blandinger deraf.
  2. 2. Fremgangsmåde ifølge krav 1, hvor katalysatoren (N-cat) er udvalgt fra gruppen bestående af eddikesyre, myresyre, trifluoreddikesyre, methansulfonsyre, ptoluensulfonsyre, HCI, HBr, H2S04, H3P04, BCI3, BF3OEt2, MgCI2, MgBr2, AICI3, ZnCI2, Cu(BF4)2, aluminosilicater, sure ionbytterharpikser, carbon behandlet med HCI, H2S04 eller HN03 og blandinger deraf.
  3. 3. Fremgangsmåde ifølge krav 1 eller 2, hvor reaktionen (N-reac) sker i et opløsningsmiddel (Nsolv); opløsningsmiddel (N-solv) er udvalgt fra gruppen bestående af vand, tert-butanol, isopropanol, acetonitril, propionitril, THF, methyFTHF, NMP, dioxan, 1,2-dimethoxyethan, dichlormethan, 1,2-dichlorethan, chloroform, toluen, benzen, chlorobenzen, hexan, cyclohexan, ethylacetat, eddikesyre, myresyre, trifluoreddikesyre og blandinger deraf.
  4. 4. Fremgangsmåde ifølge et eller flere af kravene 1 til 3, hvor forbindelse med formlen (XXII) fremstillet i et trin (O) eller i to trin, de to trin er trin (01) og trin (02); trin (O) omfatter en reaktion (O-reac); reaktion (O-reac) er en reaktion af forbindelsen med formlen (XXIII), med et reagens (O-reag);
    (XXIII) reagens (O-reag) er udvalgt fra gruppen bestående af pereddikesyre, trifluorpereddikesyre, perbenzoesyre, 3-chlorperbenzoesyre, monoperphthalsyre, dimethyldioxiran, tert-butylhydroperoxid, dibenzoylperoxid, cumenhydroperoxid, oxygen, luft, natriumhypochlorit, KHS05, Na202, vandig H202, H202 opløst i eddikesyre, H202 opløst i trifluoreddikesyre, og blandinger deraf; trin (01) omfatter en reaktion (01-reac); reaktion (01-reac) er en reaktion af forbindelsen med formlen (XXIII) med vand og med en forbindelse (01-comp); forbindelse (01-comp) er udvalgt fra gruppen bestående af brom, N-bromosuccinimid, chlor, N-chlorsuccinimid, iod, N-iodsuccinimid, IBr, BrCI, og blandinger deraf; trin (02) omfatter en reaktion (02-reac); reaktion (02-reac) er en reaktion af reaktionsproduktet fra reaktion (01-reac) med en base (02-base); base (02-base) er udvalgt fra gruppen bestående af natriumhydroxid, kaliumhydroxid, calciumhydroxid og blanding deraf.
  5. 5. Fremgangsmåde ifølge krav 4, hvor reagenset (O-reag) er udvalgt fra gruppen bestående af pereddikesyre, tert-butylhydroperoxid, oxygen, luft,
    natriumhypochlorit, vandig H202, H202 opløst i eddikesyre, H202 opløst i trifluoreddikesyre og blandinger deraf.
  6. 6. Fremgangsmåde ifølge krav 4 eller 5, hvor forbindelse med formlen (XXIII) fremstilles i et trin (P); trin (P) omfatter en reaktion (P-reac); i reaktion (P-reac) eksponeres forbindelsen med formlen (XXIV) for en temperatur (P-temp); (XXIV) temperatur (P-temp) er fra 0 til 300 °C.
  7. 7. Fremgangsmåde ifølge krav 6, hvor forbindelse med formlen (XXIV) fremstilles over tre trin, hvilke tre trin er et trin (Q1), et trin (Q2) og et trin (Q3); trin (Q1) omfatter en reaktion (Q1-reac) ved en reaktion af forbindelsen med formlen (XXV) sammen med et reagens (Q1 -reag);
    (XXV) Q er Br, Cl eller I; reagens (Q1-reag) er udvalgt fra gruppen bestående af lithium, magnesium, aluminium, zink, calcium, isopropylmagnesiumchlorid, isopropylmagnesiumbromid, butyllithium, sec-butyllithium og blandinger deraf, trin (Q2) omfatter en reaktion (Q2-reac); reaktion (Q2-reac) er en reaktion af reaktionsproduktet af reaktion (Q1-reac) med acetone; i trin (Q3) omfatter en reaktion (Q3-reac); reaktion (Q3-reac) er en reaktion af reaktionsproduktet af reaktion (Q2- reac) med et reagens (Q3-reag);
    reagens (Q3-reag) er udvalgt fra gruppen bestående af vand, methanol, ethanol, oxalsyre, citronsyre, NH4CI, HCI, HBr, HN03, H2S04, H3P04, eddikesyre, propionsyre, myresyre og blandinger deraf.
  8. 8. Anvendelse af forbindelsen med formlen (XXI) som en duft sammen med forbindelsen med formlen (XXI) som defineret i krav 1.
  9. 9. Anvendelse af forbindelsen med formlen (XXI) til fremstilling af medetomidin sammen med forbindelsen med formlen (XXI) som defineret i krav 1.
DK12784297.9T 2012-05-08 2012-11-15 Fremgangsmåde til fremstilling af 2-(2,3-dimethylphenyl)-1-propanal DK2847157T3 (da)

Applications Claiming Priority (6)

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
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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US (1) US9126915B2 (da)
EP (1) EP2847157B1 (da)
JP (1) JP5777840B2 (da)
KR (1) KR101537204B1 (da)
CN (1) CN104203893B (da)
AU (1) AU2012285676B2 (da)
CA (1) CA2866431C (da)
CL (2) CL2014002908A1 (da)
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DK (1) DK2847157T3 (da)
EA (2) EA025591B1 (da)
ES (1) ES2557638T3 (da)
HR (1) HRP20151390T1 (da)
HU (1) HUE026686T2 (da)
IN (1) IN2014DN07982A (da)
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JP5777840B2 (ja) * 2012-05-08 2015-09-09 ロンザ・リミテッド ２−（２，３−ジメチルフェニル）−１−プロパナールを調製するための方法
IN2014DN07983A (da) * 2012-05-08 2015-05-01 Lonza Ag
US9156793B2 (en) * 2012-06-28 2015-10-13 Lonza Ltd. Method for preparation of medetomidine with chloroacetone
IN2014DN08121A (da) 2012-06-28 2015-05-01 Lonza Ag
WO2016074118A1 (en) 2014-11-10 2016-05-19 Givaudan Sa Improvements in or relating to organic compounds
GB201501593D0 (en) * 2015-01-30 2015-03-18 Cambrex Karlskoga Ab New compounds and processes
US11858874B2 (en) 2020-12-21 2024-01-02 Lg Chem, Ltd. Method for preparing alpha-methylstyrene

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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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EA025591B1 (ru) 2017-01-30
CN104203893B (zh) 2016-02-03
EA201691508A1 (ru) 2016-11-30
HRP20151390T1 (hr) 2016-01-15
PT2847157E (pt) 2016-01-27
CL2014002908A1 (es) 2014-12-19
IN2014DN07982A (da) 2015-05-01
CN104203893A (zh) 2014-12-10
US9126915B2 (en) 2015-09-08
ES2557638T3 (es) 2016-01-27
JP5777840B2 (ja) 2015-09-09
HUE026686T2 (en) 2016-07-28
EA029130B1 (ru) 2018-02-28
PL2847157T3 (pl) 2016-04-29
EP2847157B1 (en) 2015-10-28
SG11201405611SA (en) 2014-11-27
CY1117404T1 (el) 2017-04-26
KR20140139076A (ko) 2014-12-04
TWI531557B (zh) 2016-05-01
CL2016001663A1 (es) 2017-01-06
MY165212A (en) 2018-03-05
CA2866431C (en) 2017-06-27
EA201400937A1 (ru) 2015-01-30
EP2847157A2 (en) 2015-03-18
CA2866431A1 (en) 2013-01-24
AU2012285676B2 (en) 2016-02-25
JP2015517473A (ja) 2015-06-22
TW201412697A (zh) 2014-04-01
NZ700641A (en) 2016-02-26
WO2013011156A2 (en) 2013-01-24
KR101537204B1 (ko) 2015-07-22
US20150080287A1 (en) 2015-03-19
HK1201060A1 (zh) 2015-08-21
WO2013011156A3 (en) 2013-04-04

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