IL40972A - Process for the preparation of(3-benzoylphenyl)alkanoic acids - Google Patents
Process for the preparation of(3-benzoylphenyl)alkanoic acidsInfo
- Publication number
- IL40972A IL40972A IL40972A IL4097272A IL40972A IL 40972 A IL40972 A IL 40972A IL 40972 A IL40972 A IL 40972A IL 4097272 A IL4097272 A IL 4097272A IL 40972 A IL40972 A IL 40972A
- Authority
- IL
- Israel
- Prior art keywords
- benzoylphenyl
- process according
- acid
- nitrile
- benzene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 14
- 239000002253 acid Substances 0.000 title claims abstract 13
- 150000007513 acids Chemical class 0.000 title claims abstract 6
- 238000002360 preparation method Methods 0.000 title claims abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract 15
- 150000002825 nitriles Chemical class 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract 2
- -1 3-chlorocarbonylphenyl Chemical group 0.000 claims 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- RGYOCHMZSLUCNP-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanenitrile Chemical compound N#CC(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 RGYOCHMZSLUCNP-UHFFFAOYSA-N 0.000 claims 1
- XXQNFMGCPMJJSJ-UHFFFAOYSA-N 3-(1-cyanoethyl)benzoyl chloride Chemical compound N#CC(C)C1=CC=CC(C(Cl)=O)=C1 XXQNFMGCPMJJSJ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000005171 halobenzenes Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1360560 Preparation of 3-benzoylphenylalkanoic acids RHONE-POULENC SA 1 Dec 1972 [3 Dec 1971 16 Oct 1972] 55640/72 Heading C2C Compounds XV in which R 4 is H or halo, and R 3 is H or CH 3 are prepared by Friedel-Crafts reaction of a nitrile XVI and benzene or a halobenzene to give a nitrile XVII which is then hydrolysed. The free acid may be converted to a salt by methods known per se. The starting material XVI is prepared by reaction of SOCl 2 with the appropriate acid.
[GB1360560A]
Claims (11)
1. Process for the preparation of (3-benzoyl-p enyl ) alkanoic acids of the general formula: (wherein represents a hydrogen atom or a methyl radical and R^ represents a hydrogen or halogen atom) which comprises carrying out a Friedel-Crafts reaction between a ( 3-chlorocarbonylphenyl)alkano-nitrile of the general formula: (wherein R^ is as hereinbefore defined) and benzene or a halogenobenzene, and hydrolysing the resulting nitrile of the general formula: (wherein R3 and R4 are as hereinbefore defined) to the corresponding (3-benzoylphenyl) alkanoic acid.
2. Process according to claim 1 in which an excess of benzene or the halogenobenzene is employed in relation to the ( 3-chlorocarbonylphenyl)alkanonitrile reactant.
3. Process according to claim 1 or 2 in which the Friedel-Crafts catalyst employed is aluminium chloride.
4. Process according to claim 1, 2 or 3 in which the reaction between the ( 3-chlorocarbonylphenyl)-alkanonitrile and benzene or a halogenobenzene is carried out at the reflux temperature of the reaction mixture.
5. Process according to any one of the preceding claims in which hydrolysis of the intermediate nitrile to the corresponding ( 3-benzoylphenyl) alkanoic acid is effected by heating the nitrile in water or an organic solvent in the presence of a base or of an acid.
6. Process according to claim 5 in which the base is sodium hydroxide or potassium hydroxide, and the acid is sulphuric acid.
7. Process according to any one of claims 1 to 6 in which a Friedel-Crafts reaction is carried out between 2-( 3-chlorocarbonylphenyl )propionitrile and benzene, and 2-(3-benzoylphenyl)propionitrile thus obtained is hydrolysed to 2-(3-benzoylphenyl)propionic acid.
8. Process according to any one of the preceding claims followed by the step of converting by methods known per se the ( 3-benzoylphenyl)alkanoic acid obtained into a metal salt or an addition salt with a nitrogenous base.
9. Process for the preparation of (3-benzoyl phenyl)alkanoic acids according to claim 1 substantially as described in Sscample 1.
10. Process for the preparation of (3-benzoyl-phenyDalkanoic acids according to claim 1 substantially as described in Example 2,
11. ( 3-Benzoylphenyl)alkanoic acids of the general formula depicted in claim 1, and metal salts and addition salts with nitrogenous bases, when prepared by the process claimed in any one of claims 1 to 10. Attorney for Applicants
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7143565A FR2163875A5 (en) | 1971-12-03 | 1971-12-03 | 3-benzoylphenyl acetic and 2-(3-benzoyl phenyl) - propionic acids prepn - for use as anti-inflammatories |
| FR7236570A FR2202873A2 (en) | 1972-10-16 | 1972-10-16 | 3-benzoylphenyl acetic and 2-(3-benzoyl phenyl) - propionic acids prepn - for use as anti-inflammatories |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40972A0 IL40972A0 (en) | 1973-01-30 |
| IL40972A true IL40972A (en) | 1976-03-31 |
Family
ID=26216758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40972A IL40972A (en) | 1971-12-03 | 1972-11-30 | Process for the preparation of(3-benzoylphenyl)alkanoic acids |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS528301B2 (en) |
| AR (1) | AR194864A1 (en) |
| AT (1) | AT321283B (en) |
| BE (1) | BE792218A (en) |
| CA (1) | CA972765A (en) |
| CH (1) | CH545761A (en) |
| CS (1) | CS170457B2 (en) |
| CY (1) | CY916A (en) |
| DD (1) | DD100239A5 (en) |
| DE (1) | DE2258985C2 (en) |
| DK (1) | DK134814B (en) |
| ES (1) | ES409237A1 (en) |
| FI (1) | FI55173C (en) |
| GB (1) | GB1360560A (en) |
| HK (1) | HK60177A (en) |
| HU (1) | HU166290B (en) |
| IE (1) | IE36936B1 (en) |
| IL (1) | IL40972A (en) |
| LU (1) | LU66586A1 (en) |
| NL (1) | NL7215990A (en) |
| NO (1) | NO139782C (en) |
| OA (1) | OA04219A (en) |
| PL (1) | PL77271B1 (en) |
| SE (1) | SE397675B (en) |
| SU (1) | SU457210A3 (en) |
| YU (1) | YU36003B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS582934B2 (en) * | 1974-07-29 | 1983-01-19 | ニツシンセイフン カブシキガイシヤ | Process for producing 2-(substituted aryl)-propionic acid |
| DE2708142C3 (en) * | 1977-02-25 | 1981-10-29 | Rütgerswerke AG, 6000 Frankfurt | Process for the preparation of substituted phenylacetonitriles and new phenylacetonitriles |
| DE3065155D1 (en) | 1979-07-16 | 1983-11-10 | Sagami Chem Res | Alpha-thio-alpha-aryl-substituted alkanonitriles, process for their preparation, process for preparing alpha-aryl-substituted alkanonitriles and the corresponding carboxylic acids therefrom and process for preparing intermediates |
| SE8400239D0 (en) * | 1984-01-19 | 1984-01-19 | Pharmacia Ab | NEW ARYLETIC ACID DERIVATIVES |
| ES2058024B1 (en) * | 1992-11-10 | 1995-05-01 | Menarini Lab | NEW ARILPROPIONIC DERIVATIVE, MANUFACTURING PROCEDURE OF THE SAME AND ITS USE AS AN ANALGESIC. |
| ES2163986B1 (en) * | 1999-07-13 | 2003-02-16 | Menarini Lab | ACIDOS-ALFA-ARILPROPIONICOS AND ARILACETICOS AS INHIBITORS OF CYCLLOXYGENASA-II. |
| CN111675631A (en) * | 2020-06-24 | 2020-09-18 | 湖北仙盛科技股份有限公司 | Synthesis process of cyano ketoprofen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1546478A (en) * | 1967-01-27 | 1968-11-22 | Rhone Poulenc Sa | New derivatives of 3-benzoylphenylacetic acid and their preparation |
| GB1226344A (en) * | 1967-07-31 | 1971-03-24 |
-
1972
- 1972-11-22 OA OA54753A patent/OA04219A/en unknown
- 1972-11-24 NL NL7215990A patent/NL7215990A/xx unknown
- 1972-11-30 IE IE1660/72A patent/IE36936B1/en unknown
- 1972-11-30 JP JP47119468A patent/JPS528301B2/ja not_active Expired
- 1972-11-30 IL IL40972A patent/IL40972A/en unknown
- 1972-12-01 HU HURO687A patent/HU166290B/hu unknown
- 1972-12-01 DK DK602072AA patent/DK134814B/en not_active IP Right Cessation
- 1972-12-01 AR AR245440A patent/AR194864A1/en active
- 1972-12-01 NO NO4425/72A patent/NO139782C/en unknown
- 1972-12-01 AT AT1022772A patent/AT321283B/en active
- 1972-12-01 SU SU1859757A patent/SU457210A3/en active
- 1972-12-01 PL PL1972159227A patent/PL77271B1/en unknown
- 1972-12-01 SE SE7215722A patent/SE397675B/en unknown
- 1972-12-01 BE BE792218D patent/BE792218A/en not_active IP Right Cessation
- 1972-12-01 CH CH1756172A patent/CH545761A/xx not_active IP Right Cessation
- 1972-12-01 DD DD167245A patent/DD100239A5/xx unknown
- 1972-12-01 GB GB5564072A patent/GB1360560A/en not_active Expired
- 1972-12-01 CY CY916A patent/CY916A/en unknown
- 1972-12-01 CA CA158,010A patent/CA972765A/en not_active Expired
- 1972-12-01 LU LU66586A patent/LU66586A1/xx unknown
- 1972-12-01 YU YU2990/72A patent/YU36003B/en unknown
- 1972-12-01 CS CS8228A patent/CS170457B2/cs unknown
- 1972-12-01 FI FI3415/72A patent/FI55173C/en active
- 1972-12-01 DE DE2258985A patent/DE2258985C2/en not_active Expired
- 1972-12-02 ES ES409237A patent/ES409237A1/en not_active Expired
-
1977
- 1977-12-01 HK HK601/77A patent/HK60177A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE36936B1 (en) | 1977-03-30 |
| NO139782B (en) | 1979-01-29 |
| FI55173C (en) | 1979-06-11 |
| AR194864A1 (en) | 1973-08-24 |
| LU66586A1 (en) | 1973-07-18 |
| SE397675B (en) | 1977-11-14 |
| SU457210A3 (en) | 1975-01-15 |
| DK134814B (en) | 1977-01-24 |
| DD100239A5 (en) | 1973-09-12 |
| CS170457B2 (en) | 1976-08-27 |
| AT321283B (en) | 1975-03-25 |
| BE792218A (en) | 1973-06-01 |
| YU36003B (en) | 1981-11-13 |
| HU166290B (en) | 1975-02-28 |
| GB1360560A (en) | 1974-07-17 |
| NO139782C (en) | 1979-05-09 |
| PL77271B1 (en) | 1975-04-30 |
| NL7215990A (en) | 1973-06-05 |
| DE2258985A1 (en) | 1973-06-14 |
| CH545761A (en) | 1974-02-15 |
| JPS528301B2 (en) | 1977-03-08 |
| CA972765A (en) | 1975-08-12 |
| IE36936L (en) | 1973-06-03 |
| DK134814C (en) | 1977-06-13 |
| ES409237A1 (en) | 1975-12-01 |
| YU299072A (en) | 1981-02-28 |
| HK60177A (en) | 1977-12-09 |
| JPS4864059A (en) | 1973-09-05 |
| IL40972A0 (en) | 1973-01-30 |
| DE2258985C2 (en) | 1982-07-01 |
| CY916A (en) | 1977-12-23 |
| OA04219A (en) | 1979-12-31 |
| FI55173B (en) | 1979-02-28 |
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