GB638196A - Improvements in or relating to the preparation of hydroxy aromatic carboxylic acids - Google Patents
Improvements in or relating to the preparation of hydroxy aromatic carboxylic acidsInfo
- Publication number
- GB638196A GB638196A GB1269848A GB1269848A GB638196A GB 638196 A GB638196 A GB 638196A GB 1269848 A GB1269848 A GB 1269848A GB 1269848 A GB1269848 A GB 1269848A GB 638196 A GB638196 A GB 638196A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ketone
- hydroxy
- water
- acid
- alkali
- 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
- -1 hydroxy aromatic carboxylic acids Chemical class 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 3
- 239000001569 carbon dioxide Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001261 hydroxy acids Chemical class 0.000 abstract 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 2
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 abstract 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 abstract 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 abstract 1
- AFIMKCDXMUVHON-UHFFFAOYSA-N 5-benzyl-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(CC=2C=CC=CC=2)=C1 AFIMKCDXMUVHON-UHFFFAOYSA-N 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-M naphthalen-1-olate Chemical compound C1=CC=C2C([O-])=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-M 0.000 abstract 1
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 1
- 150000004707 phenolate Chemical class 0.000 abstract 1
- 229940031826 phenolate Drugs 0.000 abstract 1
- 229960004889 salicylic acid Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Mono-hydroxy mono-carboxylic acids of the benzene and naphthalene series are obtained by the action of carbon dioxide on a dry solution of an alkali metal phenolate or naphtholate in a dialkyl ketone which is liquid at ordinary temperatures and has a boiling point of at least 75 DEG C. Various substituents may be present in the nucleus but at least one of the positions ortho to the hydroxy group is preferably unsubstituted. Methyl isobutyl ketone is the preferred solvent for naphthols and di-isobutyl ketone for phenol itself, these being substantially immiscible with water. The reaction is preferably carried out at least 10 degrees below the boiling point of the ketone, carbon dioxide being passed in and the di-salt of the hydroxy acid being precipitated. This is filtered off and a further portion of alkali and phenol or naphthol added, giving after dehydration a solution which may be again reacted with carbon dioxide. The free hydroxy-acid is liberated from the salt and isolated in various ways. Examples show the preparation of 1-hydroxy-2-naphthoic acid, 2-hydroxy-1-naphthoic acid, salicylic acid and 5-benzyl-salicylic acid. Specifications 384,619, 460,282, 483,795 and 511,393 are referred to. Solutions of alkali phenolates or naphtholates in dialkyl ketones are obtained by mixing a solution of the phenol or naphthol in the ketone with alkali metal, or concentrated aqueous alkali; in the latter case the water is removed by distillation. If the ketone is substantially immiscible with water, e.g. methyl isobutyl ketone, the distillate is separated and the ketone layer returned to the reaction vessel. When using water-soluble ketones such as methyl ethyl ketone, an azeotrope distils and fresh dry ketone must be added to replace that removed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1269848A GB638196A (en) | 1948-05-08 | 1948-05-08 | Improvements in or relating to the preparation of hydroxy aromatic carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1269848A GB638196A (en) | 1948-05-08 | 1948-05-08 | Improvements in or relating to the preparation of hydroxy aromatic carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB638196A true GB638196A (en) | 1950-05-31 |
Family
ID=10009464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1269848A Expired GB638196A (en) | 1948-05-08 | 1948-05-08 | Improvements in or relating to the preparation of hydroxy aromatic carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB638196A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59186942A (en) * | 1983-04-07 | 1984-10-23 | Kawasaki Kasei Chem Ltd | Purification of crude 1,4-dihydroxy-2-naphthoic acid or its salt |
-
1948
- 1948-05-08 GB GB1269848A patent/GB638196A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59186942A (en) * | 1983-04-07 | 1984-10-23 | Kawasaki Kasei Chem Ltd | Purification of crude 1,4-dihydroxy-2-naphthoic acid or its salt |
| JPH0468301B2 (en) * | 1983-04-07 | 1992-11-02 | Kawasaki Kasei Chemicals |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Tomlinson 2nd et al. | Studies on lignin and related compounds. Xxv. Mechanism of vanillin formation from spruce lignin sulfonic acids in relation to lignin structure1 | |
| GB638196A (en) | Improvements in or relating to the preparation of hydroxy aromatic carboxylic acids | |
| GB738359A (en) | Improvements in or relating to the preparation of aromatic hydroxy carboxylic acids and salts thereof | |
| Willems | The Aliphatic Hydroxysulphonic Acids and Their Internal Esters: The Sultones Part II. The Sultones | |
| GB734598A (en) | Improvements in or relating to the preparation of hydroxy aromatic carboxylic acids and salts thereof | |
| US2656382A (en) | Preparation of 2, 4-dichlorophenoxyacetic acid | |
| US2509772A (en) | Method of preparing chloroaryloxy acetic acids | |
| Balfe et al. | 82. Alkyl–oxygen fission in carboxylic esters. Part VI. Solvolytic reactions of esters of optically active cyclo hexylphenyl-, methylphenyl-, and methyl-α-naphthyl-carbinols | |
| Perkin | XV.—The determination of acetyl groups | |
| GB651670A (en) | Improvements in preparation of polychlorophenoxy-aliphatic acids | |
| Slack et al. | 337. A study of the mechanism of oxidation with chromic acid. Part II | |
| Ebel et al. | Preparation of 2, 4-D (2, 4-dichlorophenoxyacetic acid) from phenol and monochloracetic acid. | |
| DE416544C (en) | Process for the preparation of dihalodiphenylmethanedicarboxylic acids | |
| SU95525A1 (en) | Method for producing phenylacetic acid | |
| Chapman | CCCLXXXIX.—Isomeric change in aromatic compounds. Part I. The conversion of diacylanilides into acylamino-ketones | |
| Tedder et al. | 45. The direct introduction of the diazonium group into aromatic nuclie. Part V. The action of buffered nitrous acid on aromatic hydroxy-acids | |
| GB646736A (en) | Improvements in methods of preparing methyl ethers of aromatic hydroxy compounds | |
| GB400169A (en) | Improvements in or relating to the concentration of aliphatic acids | |
| GB824144A (en) | An improved process for the carboxylation of phenols | |
| GB335547A (en) | Process for the manufacture of condensation products from aldehydes and phenols | |
| Pope et al. | Synthesis of plant-growth regulators. Part III. ω-2-Naphthyloxyalkanecarboxylic acids | |
| Marshall | CCCXX.—Di iso propylmalonic acid and its derivatives | |
| Robinson et al. | 341. Experiments on the synthesis of substances related to the sterols. Part V. The condensation of phenylsuccinic anhydride with veratrole under the influence of aluminium chloride | |
| Idler et al. | The Isolation of n-Octanyl Alcohol from a Marine Tube Worm | |
| CH311529A (en) | Process for the preparation of a benzothiazole derivative. |