RU2017113180A - Способ - Google Patents

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RU2017113180A
RU2017113180A RU2017113180A RU2017113180A RU2017113180A RU 2017113180 A RU2017113180 A RU 2017113180A RU 2017113180 A RU2017113180 A RU 2017113180A RU 2017113180 A RU2017113180 A RU 2017113180A RU 2017113180 A RU2017113180 A RU 2017113180A
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Russia
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compound
functional group
formula
regioselective
introduction
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RU2017113180A
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RU2708669C2 (ru
RU2017113180A3 (ru
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Це ЧИ-ЛАМ
Мартин Алан ЛОВЧИК
Саймон ЭЛЛВУД
Андреас ГЁКЕ
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Живодан Са
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    • 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
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/307—Compounds having groups having acetal carbon atoms bound to carbon atoms of six-membered aromatic 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
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/542—Alkylated benzaldehydes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • 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
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Claims (22)

1. Региоселективное введение функциональной группы в диалкилбензольное соединение
Figure 00000001
в котором соотношение соединения, содержащего функциональную группу в положении (а), к соединению, содержащему функциональную группу в положении (b), составляет по меньшей мере 70:30, более предпочтительно по меньшей мере 80:20, еще более предпочтительно по меньшей мере 85:15 и еще более предпочтительно по меньшей мере 90:10, отличающееся тем, что заместитель R представляет собой изобутильную группу.
2. Региоселективное введение функциональной группы по п. 1, в котором реакция представляет собой реакцию карбонилирования с введением бензальдегидной функциональной группы в положение (а).
3. Региоселективное карбонилирование по п. 2, в котором реакцию карбонилирования проводят при использовании HF/BF3 и монооксида углерода.
4. Способ получения соединения формулы (I)
Figure 00000002
включающий стадию региоселектиивного введения функциональной группы в диалкилбензольное соединение
Figure 00000003
в котором соотношение соединения, содержащего функциональную группу в положении (а), к соединению, содержащему функциональную группу в положении (b), составляет по меньшей мере 70:30, более предпочтительно по меньшей мере 80:20, еще более предпочтительно по меньшей мере 85:15 и еще более предпочтительно по меньшей мере 90:10, и в котором заместитель R представляет собой изобутильную группу.
5. Способ получения соединения формулы (I)
Figure 00000004
включающий стадии:
А)
Figure 00000005
В)
Figure 00000006
и
С) гидрирования соединения (VI) с получением соединения (I).
6. Способ по п. 5, в котором соединение (III) превращают в соответствующий диалкилацеталь для очистки и затем дополнительно превращают в соединение (I).
7. Соединение формулы IIIb
Figure 00000007
которое применяют в качестве промежуточного соединения в способе получения соединения формулы (I).
RU2017113180A 2014-11-12 2015-11-12 Способ получения 3-(4-изобутил-2-метилфенил)пропаналя, используемого в парфюмерной промышленности RU2708669C2 (ru)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB1420111.5A GB201420111D0 (en) 2014-11-12 2014-11-12 Process
GB1420111.5 2014-11-12
PCT/EP2015/076471 WO2016075257A1 (en) 2014-11-12 2015-11-12 Process

Publications (3)

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RU2017113180A true RU2017113180A (ru) 2018-12-13
RU2017113180A3 RU2017113180A3 (ru) 2019-04-10
RU2708669C2 RU2708669C2 (ru) 2019-12-11

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Country Status (12)

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US (1) US10760033B2 (ru)
EP (1) EP3089956B1 (ru)
JP (1) JP6728164B2 (ru)
CN (1) CN107001192A (ru)
BR (1) BR112017007197B1 (ru)
CO (1) CO2017005417A2 (ru)
ES (1) ES2754351T3 (ru)
GB (1) GB201420111D0 (ru)
MX (1) MX2017004872A (ru)
RU (1) RU2708669C2 (ru)
SG (1) SG11201703003VA (ru)
WO (1) WO2016075257A1 (ru)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4019490B1 (en) * 2019-08-23 2023-11-01 Mitsubishi Gas Chemical Company, Inc. Method for producing m-dialkylbenzaldehyde
TW202124347A (zh) * 2019-10-17 2021-07-01 日商三菱瓦斯化學股份有限公司 ２，４—二烷基苯甲醛之製造方法
WO2021075517A1 (ja) 2019-10-17 2021-04-22 三菱瓦斯化学株式会社 アルデヒド化合物及びその製造方法、並びに香料組成物
WO2023053860A1 (ja) * 2021-09-29 2023-04-06 三菱瓦斯化学株式会社 アルデヒド組成物

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1364620A (fr) * 1963-03-15 1964-06-26 Rhone Poulenc Sa Aldéhyde p. isobutyldihydrocinnamique
BE672280A (ru) 1964-11-13 1966-05-12
CA1211754A (en) 1980-07-09 1986-09-23 David Webb Process for the production of phenyl substituted alcohols
DE4106661A1 (de) * 1991-03-02 1992-09-03 Basf Ag 2-methylbenzaldehyddialkylacetale
US5527769A (en) 1993-05-26 1996-06-18 Firmenich Sa Aromatic compounds and their use in perfumery
WO2000015593A2 (en) * 1998-09-10 2000-03-23 Exxon Chemical Patents Inc. Process for making aromatic aldehydes
JP4667761B2 (ja) * 2004-04-02 2011-04-13 出光興産株式会社 冷凍機油組成物
FR2880884B1 (fr) 2005-01-19 2007-04-20 Mane Fils Sa V Nouveaux composes odorants, procede de synthese et utilisations
DE102009001569A1 (de) * 2009-03-16 2010-09-23 Henkel Ag & Co. Kgaa Lilial-Substitut
GB201308248D0 (en) * 2013-05-08 2013-06-12 Givaudan Sa Improvements in or relating to organic compounds
GB201308236D0 (en) * 2013-05-08 2013-06-12 Givaudan Sa Improvements in or relating to organic compounds

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ES2754351T3 (es) 2020-04-17
JP6728164B2 (ja) 2020-07-22
RU2708669C2 (ru) 2019-12-11
GB201420111D0 (en) 2014-12-24
CN107001192A (zh) 2017-08-01
US10760033B2 (en) 2020-09-01
US20180282662A1 (en) 2018-10-04
CO2017005417A2 (es) 2017-08-31
SG11201703003VA (en) 2017-05-30
EP3089956B1 (en) 2019-08-07
BR112017007197A2 (pt) 2017-12-12
EP3089956A1 (en) 2016-11-09
WO2016075257A1 (en) 2016-05-19
JP2017533926A (ja) 2017-11-16
BR112017007197B1 (pt) 2021-07-06
MX2017004872A (es) 2017-07-04
RU2017113180A3 (ru) 2019-04-10

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