GB690816A - Improvements in or relating to the manufacture of substituted phenoxy acetic acids - Google Patents
Improvements in or relating to the manufacture of substituted phenoxy acetic acidsInfo
- Publication number
- GB690816A GB690816A GB5050A GB5050A GB690816A GB 690816 A GB690816 A GB 690816A GB 5050 A GB5050 A GB 5050A GB 5050 A GB5050 A GB 5050A GB 690816 A GB690816 A GB 690816A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- chloro
- acid
- phenol
- acetic acid
- 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.)
- Expired
Links
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 abstract 1
- BUZGTPXEOMENFN-UHFFFAOYSA-N 2-(2-benzyl-4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CC1=CC=CC=C1 BUZGTPXEOMENFN-UHFFFAOYSA-N 0.000 abstract 1
- NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 abstract 1
- BQLUUGXNYOGDMW-UHFFFAOYSA-N 2-phenoxy-3-phenylpropanoic acid Chemical class C=1C=CC=CC=1OC(C(=O)O)CC1=CC=CC=C1 BQLUUGXNYOGDMW-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The Specification comprises substituted benzyl phenoxy-acetic acids of the formula <FORM:0690816/IV (b)/1> wherein R represents a chlorine atom or a methyl or ethyl group and R1 and R2 each represent a hydrogen or chlorine atom or a methyl or ethyl group. They may be prepared by reacting in a solvent the alkali metal salt of the appropriate phenol and the alkali metal salt of chloracetic acid or an ester of chloracetic acid and where an ester is employed, hydrolysing the resultant esterified acid. Suitable solvents are water, alcohol and toluene. The phenol may be obtained by the process of Specifications 669,072 or 667,403. Examples describe the preparation of (1) 2-benzyl-p-chlorophenoxy acetic acid by reaction of chloracetic acid and p-chloro-o-benzyl phenol in aqueous alcoholic potassium hydroxide; (2) 2-benzyl-4-chloro-3 : 5-dimethyl phenoxy acetic acid by reaction in anhydrous alcohol of 2-benzyl-4-chloro-3 : 5-xylen-1-ol and ethyl chloro-acetate in the presence of sodium, followed by refluxing with caustic potash; (3) 2-benzyl-4 : 6-dichloro-phenoxy acetic acid is prepared similarly.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5050A GB690816A (en) | 1950-01-02 | 1950-01-02 | Improvements in or relating to the manufacture of substituted phenoxy acetic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5050A GB690816A (en) | 1950-01-02 | 1950-01-02 | Improvements in or relating to the manufacture of substituted phenoxy acetic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB690816A true GB690816A (en) | 1953-04-29 |
Family
ID=9697504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5050A Expired GB690816A (en) | 1950-01-02 | 1950-01-02 | Improvements in or relating to the manufacture of substituted phenoxy acetic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB690816A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3054823A (en) * | 1962-09-18 | Production of aryloxy fatty acids | ||
| US8003703B2 (en) | 2003-08-21 | 2011-08-23 | Astrazeneca Ab | Phenoxiacetic acid derivatives |
| US8008350B2 (en) | 2005-10-06 | 2011-08-30 | Astrazeneca Ab | Biphenyloxyacetic acid derivatives for the treatment of respiratory disease |
| US8022248B2 (en) | 2004-07-08 | 2011-09-20 | Astrazeneca Ab | Substituted acids for the treatment of respiratory diseases |
| US8148572B2 (en) | 2005-10-06 | 2012-04-03 | Astrazeneca Ab | Compounds |
| US8158820B2 (en) | 2003-04-07 | 2012-04-17 | Astrazeneca Ab | Compounds |
| US8163727B2 (en) | 2004-08-24 | 2012-04-24 | Astrazeneca Ab | Biphenyloxyacetic acid derivatives for the treatment of respiratory disease |
| US8524715B2 (en) | 2004-11-23 | 2013-09-03 | Astrazeneca Ab | Phenoxyacetic acid derivatives useful for treating respiratory diseases |
-
1950
- 1950-01-02 GB GB5050A patent/GB690816A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3054823A (en) * | 1962-09-18 | Production of aryloxy fatty acids | ||
| US8158820B2 (en) | 2003-04-07 | 2012-04-17 | Astrazeneca Ab | Compounds |
| US8003703B2 (en) | 2003-08-21 | 2011-08-23 | Astrazeneca Ab | Phenoxiacetic acid derivatives |
| US8394986B2 (en) | 2003-08-21 | 2013-03-12 | Astrazeneca Ab | Phenoxiacetic acid derivatives |
| US8022248B2 (en) | 2004-07-08 | 2011-09-20 | Astrazeneca Ab | Substituted acids for the treatment of respiratory diseases |
| US8163727B2 (en) | 2004-08-24 | 2012-04-24 | Astrazeneca Ab | Biphenyloxyacetic acid derivatives for the treatment of respiratory disease |
| US8722741B2 (en) | 2004-08-24 | 2014-05-13 | Astrazeneca Ab | Biphenyloxyacetic acid derivatives for the treatment of respiratory disease |
| US8524715B2 (en) | 2004-11-23 | 2013-09-03 | Astrazeneca Ab | Phenoxyacetic acid derivatives useful for treating respiratory diseases |
| US8008350B2 (en) | 2005-10-06 | 2011-08-30 | Astrazeneca Ab | Biphenyloxyacetic acid derivatives for the treatment of respiratory disease |
| US8148572B2 (en) | 2005-10-06 | 2012-04-03 | Astrazeneca Ab | Compounds |
| US8349897B2 (en) | 2005-10-06 | 2013-01-08 | Astrazeneca Ab | Biphenyloxyacetic acid derivatives for the treatment of respiratory disease |
| US8415394B2 (en) | 2005-10-06 | 2013-04-09 | Astrazeneca Ab | Biphenyloxyacetic acid derivatives for the treatment of respiratory disease |
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