CA2477862A1 - Improved process for the manufacture of 4-(6-bromohexyloxy)-butylbenzene - Google Patents
Improved process for the manufacture of 4-(6-bromohexyloxy)-butylbenzene Download PDFInfo
- Publication number
- CA2477862A1 CA2477862A1 CA002477862A CA2477862A CA2477862A1 CA 2477862 A1 CA2477862 A1 CA 2477862A1 CA 002477862 A CA002477862 A CA 002477862A CA 2477862 A CA2477862 A CA 2477862A CA 2477862 A1 CA2477862 A1 CA 2477862A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- phenylbutanol
- diluent
- transfer catalyst
- phase transfer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to an improved method for producing 4-(6-bromohexyloxy) butylbenzene by reacting 4-phenylbutanol with 1,6-dibromohexane in the presence of a base and a phase transfer catalyst. 4-phenylbutanol is metered in a diluent to a mixture consisting of 1,6-dibromohexane, a base, a phase transfer catalyst, and a diluent. Also disclosed is the use of the resulting 4-(6-bromohexyloxy) butylbenzene for producing salmeterol in a previously known manner.
Claims (15)
1. Improved process for preparing 4-(6-bromohexyloxy)-butylbenzene by reacting phenylbutanol with 1,6-dibromohexane in the presence of a base and a phase transfer catalyst, characterised in that 4-phenylbutanol in a diluent is metered into a mixture consisting of 1,6-dibromohexane, a base, a phase transfer catalyst and a diluent.
2. Process according to claim 1, characterised in that powdered potassium hydroxide is used as the base.
3. Process according to claim 1 or 2, characterised in that a tetraalkylammonium or tetraalkylphosphonium salt is used as the phase transfer catalyst.
4. Process according to claim 3, characterised in that a tetraalkylammonium hydrogen sulphate is used as the phase transfer catalyst.
5. Process according to one of claims 1 to 4, characterised in that an aromatic hydrocarbon or an optionally halogenated aliphatic hydrocarbon is used as diluent.
6. Process according to claim 5, characterised in that toluene or dichloromethane is used as diluent.
7. Process according to one of claims 1 to 6, characterised in that the reaction is carried out in a temperature range from -10°C to +30°C.
8. Process according to one of claims 1 to 7, characterised in that the 4-phenylbutanol is added within 10 to 240 minutes and the resulting reaction mixture is stirred for a further 30 to 180 minutes.
9. Process according to one of claims 1 to 8, characterised in that 0.75 to 2.5 equivalents of 1,6-dibromohexane are used, based on 1 equivalent of 4-phenylbutanol.
10. Process according to one of claims 1 to 9, characterised in that 2.5 to 5.5 equivalents of base are used, based on 1 equivalent of 4-phenylbutanol.
11. Process according to one of claims 1 to 10, characterised in that 0.01 to 0.5 equivalents of phase transfer catalyst are used, based on 1 equivalent of 4-phenylbutanol.
12. Process according to one of claims 1 to 11, characterised in that the mixture of 1,6-dibromohexane, a base, a phase transfer catalyst and a diluent contains 1.5 to 4.0 parts by volume of diluent, based on 1 part of 1,6-dibromohexane.
13. Process according to one of claims 1 to 12, characterised in that the mixture of 4-phenylbutanol and diluent contains 1.5 to 10 parts by volume of diluent, based on 1 part of 4-phenylbutanol.
14. Process according to one of claims 1 to 13, characterised in that after the reaction has ended water is added to the reaction mixture, the phases are separated, the organic phase is washed with water, concentrated under reduced pressure and the residue is fractionally distilled under high vacuum.
15. Process for preparing salmeterol, characterised in that the educt 4-(6-bromohexyloxy)-butylbenzene is prepared according to one of claims 1 to 14 and further processed in a manner known per se.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10209583.3 | 2002-03-05 | ||
| DE10209583A DE10209583B4 (en) | 2002-03-05 | 2002-03-05 | Process for the preparation of 4- (6-bromohexyloxy) -butylbenzene |
| PCT/EP2003/002054 WO2003074458A1 (en) | 2002-03-05 | 2003-02-28 | Improved method for the production of 4-(6-bromohexyloxy) butylbenzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2477862A1 true CA2477862A1 (en) | 2003-09-12 |
| CA2477862C CA2477862C (en) | 2011-04-05 |
Family
ID=27770986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2477862A Expired - Lifetime CA2477862C (en) | 2002-03-05 | 2003-02-28 | Improved process for the manufacture of 4-(6-bromohexyloxy)-butylbenzene |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1483226B1 (en) |
| JP (1) | JP4424992B2 (en) |
| AT (1) | ATE303981T1 (en) |
| AU (1) | AU2003227527A1 (en) |
| CA (1) | CA2477862C (en) |
| DE (2) | DE10209583B4 (en) |
| ES (1) | ES2248747T3 (en) |
| IL (2) | IL163698A0 (en) |
| WO (1) | WO2003074458A1 (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZW6584A1 (en) * | 1983-04-18 | 1985-04-17 | Glaxo Group Ltd | Phenethanolamine derivatives |
| WO1995019336A1 (en) * | 1994-01-12 | 1995-07-20 | Iovis Biomedical And Pharmaceutical Consultants | PHENYL ETHANOL AMINE ETHERS AND USES THEREOF AS β-ADRENO-RECEPTOR AGONISTS |
| ES2142771B1 (en) * | 1998-09-28 | 2001-01-01 | Vita Invest Sa | NEW DERIVATIVES OF 6- (4-PHENYL-BUTOXI) HEXYLAMINE AND PROCEDURE FOR OBTAINING SALMETEROL. |
-
2002
- 2002-03-05 DE DE10209583A patent/DE10209583B4/en not_active Expired - Lifetime
-
2003
- 2003-02-28 WO PCT/EP2003/002054 patent/WO2003074458A1/en active IP Right Grant
- 2003-02-28 AT AT03724908T patent/ATE303981T1/en active
- 2003-02-28 JP JP2003572931A patent/JP4424992B2/en not_active Expired - Lifetime
- 2003-02-28 AU AU2003227527A patent/AU2003227527A1/en not_active Abandoned
- 2003-02-28 DE DE50301150T patent/DE50301150D1/en not_active Expired - Lifetime
- 2003-02-28 CA CA2477862A patent/CA2477862C/en not_active Expired - Lifetime
- 2003-02-28 EP EP03724908A patent/EP1483226B1/en not_active Expired - Lifetime
- 2003-02-28 ES ES03724908T patent/ES2248747T3/en not_active Expired - Lifetime
- 2003-02-28 IL IL16369803A patent/IL163698A0/en unknown
-
2004
- 2004-08-24 IL IL163698A patent/IL163698A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| CA2477862C (en) | 2011-04-05 |
| DE50301150D1 (en) | 2005-10-13 |
| AU2003227527A1 (en) | 2003-09-16 |
| JP4424992B2 (en) | 2010-03-03 |
| JP2005526742A (en) | 2005-09-08 |
| DE10209583B4 (en) | 2006-01-19 |
| WO2003074458A1 (en) | 2003-09-12 |
| ES2248747T3 (en) | 2006-03-16 |
| IL163698A (en) | 2010-11-30 |
| IL163698A0 (en) | 2005-12-18 |
| EP1483226A1 (en) | 2004-12-08 |
| DE10209583A1 (en) | 2003-09-25 |
| ATE303981T1 (en) | 2005-09-15 |
| EP1483226B1 (en) | 2005-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20230228 |