WO2011048068A2 - Verfahren zur herstellung m-substituierter phenylalkanole durch isomerisierung - Google Patents
Verfahren zur herstellung m-substituierter phenylalkanole durch isomerisierung Download PDFInfo
- Publication number
- WO2011048068A2 WO2011048068A2 PCT/EP2010/065673 EP2010065673W WO2011048068A2 WO 2011048068 A2 WO2011048068 A2 WO 2011048068A2 EP 2010065673 W EP2010065673 W EP 2010065673W WO 2011048068 A2 WO2011048068 A2 WO 2011048068A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- substituted
- methyl
- tert
- propanol
- Prior art date
Links
- 0 Cc1ccc(C(*)(*)*)cc1 Chemical compound Cc1ccc(C(*)(*)*)cc1 0.000 description 2
- XQAFLLQASZCOBX-UHFFFAOYSA-N CC(C)Cc1cc(CC(C)C=O)ccc1 Chemical compound CC(C)Cc1cc(CC(C)C=O)ccc1 XQAFLLQASZCOBX-UHFFFAOYSA-N 0.000 description 1
- SGVBCLGVIOFAFT-UHFFFAOYSA-N CC(Cc1ccc(C)cc1)C=O Chemical compound CC(Cc1ccc(C)cc1)C=O SGVBCLGVIOFAFT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- 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
Definitions
- WO 2008/053148 describes a 3-stage synthesis for preparing 3- (3-tert-butylphenyl) propanal starting from 1-tert-butyl-3-ethylbenzene.
- the starting compound is first brominated to 1-tert-butyl-3- (1-bromo-ethyl) benzene and then eliminated to the corresponding substituted styrene.
- Hydroformylation then gives the 3- (3-tert-butylphenyl) propanal.
- this synthesis seems less suitable because of low yields.
- the m / p ratio is 56/44 (for 2-methyl-3- (3-tert-butylphenyl) propanal) or 51/40 (for 2-methyl-3- (3 iso-butylphenyl) propanal).
- This process also appears less suitable for a large-scale process, since the amount of expensive catalyst used is high and the selectivity to the m-isomer is low.
- EP 0 045 571 discloses the Friedel-Crafts alkylation of 2-methyl-3-phenylpropanol to 2-methyl-3- (3-tert-butylphenyl) propanol and 2-methyl-3- (4-tert-butylphenyl) propanol described.
- the alkylating reagents used are isobutylene, diisobutylene and tert-butyl chloride.
- the catalysts used are iron chloride and phosphoric acid and as solvent methylene chloride or phosphoric acid. Depending on the reaction conditions and the catalyst, m / p ratios of 1/13 to 1/5 are obtained. Total yields (m-isomer and p-isomer) are up to 52%.
- the process according to the invention makes it possible to produce the m-substituted phenylalkanols, which serve as precursors for the very interesting correspondingly substituted phenylalkanals, in the simplest manner, in a cost-effective manner and in good yield.
- the present invention relates to a process for the preparation of substituted in m-position phenylalkanols, which can be obtained by isomerization of substituted in p-position phenylalkanols.
- the isomerization takes place on certain Friedel-Crafts catalysts.
- the invention thus provides a process for the preparation of m-substituted phenylalkanols of the formula (I)
- R 1 is C 1 -C 5 -alkyl and R 2 , R 3 , R 4 and R 5, independently of one another, denote hydrogen or methyl, which is characterized in that a p-substituted phenylalkanol of the formula (II)
- Ri, R2, R3, R4 and R5 are as specified under formula (I), in the presence of a Friedel-Crafts catalyst to form an m-substituted phenylalkanol of formula (I) is isomerized.
- m / p isomer ratios of> 1/1 can be obtained under certain conditions in the isomerization reaction of p-substituted phenylalkanols to m-substituted phenylalkanols.
- Suitable alkyl radicals Ri are, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl.
- Preferred alkyl radicals Ri are: ethyl, isopropyl, isobutyl and tert-butyl. Preference is given to a process for preparing m-substituted phenylpropanols of the formula (II I)
- R 1, R 2 , R 3 , R 4 and R 5 have the meanings given under formula (I), which is characterized in that a p-substituted phenylpropanol of the formula (IV)
- R1, R2, R3, R4 and R5 are as specified under formula (I), is isomerized in the presence of a Friedel-Crafts catalyst to form an m-substituted phenylalkanol of formula (III).
- R 1 is ethyl, isopropyl, isobutyl or tert-butyl.
- R1 and R2 have the meanings given under formula (I).
- R 1 is ethyl, isopropyl, isobutyl or tert-butyl.
- a very particularly preferred process is characterized in that 2-methyl-3- (4-tert-butylphenyl) propanol is used as the starting compound in the presence of a Friedel-Crafts catalyst, in particular in the presence of aluminum trichloride (AICI3), to form 2-methyl- 3- (3-tert-butylphenyl) propanol isomerized.
- AICI3 aluminum trichloride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10768923.4A EP2490993B1 (de) | 2009-10-23 | 2010-10-19 | Verfahren zur herstellung m-substituierter phenylalkanole durch isomerisierung |
JP2012534659A JP5758906B2 (ja) | 2009-10-23 | 2010-10-19 | 異性化によるm−置換フェニルアルカノールの製造方法 |
MX2012004532A MX2012004532A (es) | 2009-10-23 | 2010-10-19 | Metodo para producir fenilalcanoles m - sustituidos por medio de isomerizacion. |
US13/503,488 US8686193B2 (en) | 2009-10-23 | 2010-10-19 | Method for producing M-substituted phenylalkanols by means of isomerization |
CN201080047752.3A CN102596870B (zh) | 2009-10-23 | 2010-10-19 | 借助异构化制备间位取代苯基链烷醇的方法 |
ES10768923.4T ES2487217T3 (es) | 2009-10-23 | 2010-10-19 | Procedimiento para la preparación de fenilalcanoles m-sustituidos mediante isomerización |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09173907 | 2009-10-23 | ||
EP09173907.8 | 2009-10-23 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2011048068A2 true WO2011048068A2 (de) | 2011-04-28 |
WO2011048068A3 WO2011048068A3 (de) | 2011-07-07 |
Family
ID=43502856
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2010/065673 WO2011048068A2 (de) | 2009-10-23 | 2010-10-19 | Verfahren zur herstellung m-substituierter phenylalkanole durch isomerisierung |
Country Status (7)
Country | Link |
---|---|
US (1) | US8686193B2 (de) |
EP (1) | EP2490993B1 (de) |
JP (1) | JP5758906B2 (de) |
CN (1) | CN102596870B (de) |
ES (1) | ES2487217T3 (de) |
MX (1) | MX2012004532A (de) |
WO (1) | WO2011048068A2 (de) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8367875B2 (en) | 2010-02-11 | 2013-02-05 | Basf Se | Process for the preparation of m-substituted alkyltoluenes by isomerization with ionic liquids as catalysts |
US8609903B2 (en) | 2010-04-01 | 2013-12-17 | Basf Se | Process for preparing hydroxy-substituted aromatic aldehydes |
US8692025B2 (en) | 2009-10-23 | 2014-04-08 | Basf Se | Process for preparing M- or P-substituted phenylalkanols by alkylation |
WO2014207205A1 (en) * | 2013-06-28 | 2014-12-31 | Givaudan Sa | Organic compounds |
US9254329B2 (en) | 2009-10-28 | 2016-02-09 | Basf Se | Stable protective coatings for pharmaceutical dosage forms |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB201308236D0 (en) | 2013-05-08 | 2013-06-12 | Givaudan Sa | Improvements in or relating to organic compounds |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2952719A1 (de) | 1979-12-29 | 1981-07-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von p-substituierten phenylpropanolen und deren estern |
EP0045571A1 (de) | 1980-07-09 | 1982-02-10 | BUSH BOAKE ALLEN Limited | Verfahren zur Herstellung phenylsubstituierter Aldehyde und phenylsubstituierter Alkohole |
WO2008053148A1 (en) | 2006-11-04 | 2008-05-08 | Givaudan Nederland Services B.V. | Novel fragrance compounds |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3856869A (en) * | 1973-06-01 | 1974-12-24 | Givaudan Corp | Process for 6-isopropyl-1, 1, 4-trimethylindan |
CA1211754A (en) * | 1980-07-09 | 1986-09-23 | David Webb | Process for the production of phenyl substituted alcohols |
DE3716730A1 (de) * | 1987-05-19 | 1988-12-01 | Basf Ag | 4-methyl-4-phenyl-1-pentanale, deren herstellung und verwendung als riechstoffe |
JP2586647B2 (ja) * | 1988-06-24 | 1997-03-05 | 住友化学工業株式会社 | p―体を高含量とするジアルキルベンゼンの製造方法 |
JP2526637B2 (ja) | 1988-06-28 | 1996-08-21 | 住友化学工業株式会社 | p−体を高含量とするジアルキルベンゼンの製造法 |
JPH02238097A (ja) | 1989-03-10 | 1990-09-20 | Kuraray Co Ltd | 香料組成物 |
US6013618A (en) * | 1997-04-24 | 2000-01-11 | Procter & Gamble Company | Perfumes having odor longevity benefits |
CA2731195C (en) | 2008-08-01 | 2016-09-13 | Basf Se | Method for producing phenylalkane-1-ols |
CN102574757B (zh) * | 2009-10-23 | 2015-12-02 | 巴斯夫欧洲公司 | 通过烷基化制备间-或对取代苯基链烷醇的方法 |
-
2010
- 2010-10-19 CN CN201080047752.3A patent/CN102596870B/zh not_active Expired - Fee Related
- 2010-10-19 MX MX2012004532A patent/MX2012004532A/es active IP Right Grant
- 2010-10-19 WO PCT/EP2010/065673 patent/WO2011048068A2/de active Application Filing
- 2010-10-19 ES ES10768923.4T patent/ES2487217T3/es active Active
- 2010-10-19 EP EP10768923.4A patent/EP2490993B1/de not_active Not-in-force
- 2010-10-19 JP JP2012534659A patent/JP5758906B2/ja not_active Expired - Fee Related
- 2010-10-19 US US13/503,488 patent/US8686193B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2952719A1 (de) | 1979-12-29 | 1981-07-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von p-substituierten phenylpropanolen und deren estern |
EP0045571A1 (de) | 1980-07-09 | 1982-02-10 | BUSH BOAKE ALLEN Limited | Verfahren zur Herstellung phenylsubstituierter Aldehyde und phenylsubstituierter Alkohole |
WO2008053148A1 (en) | 2006-11-04 | 2008-05-08 | Givaudan Nederland Services B.V. | Novel fragrance compounds |
Non-Patent Citations (1)
Title |
---|
ISHII ET AL., J. ORG. CHEM., vol. 70, 2005, pages 5471 - 5474 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8692025B2 (en) | 2009-10-23 | 2014-04-08 | Basf Se | Process for preparing M- or P-substituted phenylalkanols by alkylation |
US9254329B2 (en) | 2009-10-28 | 2016-02-09 | Basf Se | Stable protective coatings for pharmaceutical dosage forms |
US8367875B2 (en) | 2010-02-11 | 2013-02-05 | Basf Se | Process for the preparation of m-substituted alkyltoluenes by isomerization with ionic liquids as catalysts |
US8609903B2 (en) | 2010-04-01 | 2013-12-17 | Basf Se | Process for preparing hydroxy-substituted aromatic aldehydes |
WO2014207205A1 (en) * | 2013-06-28 | 2014-12-31 | Givaudan Sa | Organic compounds |
US9708570B2 (en) | 2013-06-28 | 2017-07-18 | Givaudan, S.A. | Organic compounds |
Also Published As
Publication number | Publication date |
---|---|
EP2490993A2 (de) | 2012-08-29 |
CN102596870B (zh) | 2014-11-05 |
ES2487217T3 (es) | 2014-08-20 |
US20120209031A1 (en) | 2012-08-16 |
EP2490993B1 (de) | 2014-06-11 |
WO2011048068A3 (de) | 2011-07-07 |
CN102596870A (zh) | 2012-07-18 |
JP5758906B2 (ja) | 2015-08-05 |
US8686193B2 (en) | 2014-04-01 |
JP2013508331A (ja) | 2013-03-07 |
MX2012004532A (es) | 2012-06-08 |
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