RU2017113180A - Способ - Google Patents
Способ Download PDFInfo
- Publication number
- 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
- Authority
- RU
- Russia
- Prior art keywords
- compound
- functional group
- formula
- regioselective
- introduction
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000524 functional group Chemical group 0.000 claims 7
- 238000005810 carbonylation reaction Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 230000006315 carbonylation Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Claims (22)
1. Региоселективное введение функциональной группы в диалкилбензольное соединение
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)
включающий стадию региоселектиивного введения функциональной группы в диалкилбензольное соединение
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)
включающий стадии:
А)
В)
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
которое применяют в качестве промежуточного соединения в способе получения соединения формулы (I).
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)
| Publication Number | Publication Date |
|---|---|
| RU2017113180A true RU2017113180A (ru) | 2018-12-13 |
| RU2017113180A3 RU2017113180A3 (ru) | 2019-04-10 |
| RU2708669C2 RU2708669C2 (ru) | 2019-12-11 |
Family
ID=52118369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017113180A RU2708669C2 (ru) | 2014-11-12 | 2015-11-12 | Способ получения 3-(4-изобутил-2-метилфенил)пропаналя, используемого в парфюмерной промышленности |
Country Status (12)
| Country | Link |
|---|---|
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220050137A (ko) | 2019-08-23 | 2022-04-22 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | m-디알킬벤즈알데히드의 제조방법 |
| KR20220082824A (ko) | 2019-10-17 | 2022-06-17 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 2,4-디알킬벤즈알데히드의 제조방법 |
| 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)
| 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 |
| JP4055864B2 (ja) * | 1993-05-26 | 2008-03-05 | フィルメニッヒ ソシエテ アノニム | 新規芳香族化合物及び香料製造におけるその使用 |
| US6320083B1 (en) * | 1998-09-10 | 2001-11-20 | Exxonmobil Chemical Co. | Process for making aromatic aldehydes using ionic liquids |
| 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 |
-
2014
- 2014-11-12 GB GBGB1420111.5A patent/GB201420111D0/en not_active Ceased
-
2015
- 2015-11-12 CN CN201580061201.5A patent/CN107001192A/zh active Pending
- 2015-11-12 EP EP15793851.5A patent/EP3089956B1/en active Active
- 2015-11-12 ES ES15793851T patent/ES2754351T3/es active Active
- 2015-11-12 SG SG11201703003VA patent/SG11201703003VA/en unknown
- 2015-11-12 RU RU2017113180A patent/RU2708669C2/ru active
- 2015-11-12 WO PCT/EP2015/076471 patent/WO2016075257A1/en not_active Ceased
- 2015-11-12 JP JP2017525545A patent/JP6728164B2/ja active Active
- 2015-11-12 US US15/516,602 patent/US10760033B2/en active Active
- 2015-11-12 BR BR112017007197-5A patent/BR112017007197B1/pt active IP Right Grant
- 2015-11-12 MX MX2017004872A patent/MX2017004872A/es unknown
-
2017
- 2017-05-30 CO CONC2017/0005417A patent/CO2017005417A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3089956A1 (en) | 2016-11-09 |
| ES2754351T3 (es) | 2020-04-17 |
| WO2016075257A1 (en) | 2016-05-19 |
| JP6728164B2 (ja) | 2020-07-22 |
| BR112017007197B1 (pt) | 2021-07-06 |
| RU2708669C2 (ru) | 2019-12-11 |
| RU2017113180A3 (ru) | 2019-04-10 |
| CN107001192A (zh) | 2017-08-01 |
| US10760033B2 (en) | 2020-09-01 |
| MX2017004872A (es) | 2017-07-04 |
| CO2017005417A2 (es) | 2017-08-31 |
| GB201420111D0 (en) | 2014-12-24 |
| EP3089956B1 (en) | 2019-08-07 |
| US20180282662A1 (en) | 2018-10-04 |
| JP2017533926A (ja) | 2017-11-16 |
| SG11201703003VA (en) | 2017-05-30 |
| BR112017007197A2 (pt) | 2017-12-12 |
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