CS226031B2 - Method of preparing 3-methyl-2-p-chlorophenylbutyronitrile - Google Patents
Method of preparing 3-methyl-2-p-chlorophenylbutyronitrile Download PDFInfo
- Publication number
- CS226031B2 CS226031B2 CS815676A CS567681A CS226031B2 CS 226031 B2 CS226031 B2 CS 226031B2 CS 815676 A CS815676 A CS 815676A CS 567681 A CS567681 A CS 567681A CS 226031 B2 CS226031 B2 CS 226031B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- chlorophenylbutyronitrile
- preparing
- formula
- phase transfer
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- RBGSZIRWNWQDOK-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanenitrile Chemical compound CC(C)C(C#N)C1=CC=C(Cl)C=C1 RBGSZIRWNWQDOK-UHFFFAOYSA-N 0.000 title description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- DVUVKWLUHXXIHK-UHFFFAOYSA-N tetraazanium;tetrahydroxide Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[OH-].[OH-].[OH-].[OH-] DVUVKWLUHXXIHK-UHFFFAOYSA-N 0.000 claims 1
- 230000000895 acaricidal effect Effects 0.000 abstract description 2
- 239000000642 acaricide Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- BWPYAVCZZUTOBY-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(Cl)C=C1 BWPYAVCZZUTOBY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- SWWHCQCMVCPLEQ-UHFFFAOYSA-N propan-2-yl methanesulfonate Chemical compound CC(C)OS(C)(=O)=O SWWHCQCMVCPLEQ-UHFFFAOYSA-N 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- -1 ( ± ) -cyano- (3-phenoxyphenyl) methyl (S) -3-methyl-2- (4-chlorophenyl) butanoic acid Chemical compound 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17279080A | 1980-07-28 | 1980-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS226031B2 true CS226031B2 (en) | 1984-03-19 |
Family
ID=22629252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS815676A CS226031B2 (en) | 1980-07-28 | 1981-07-24 | Method of preparing 3-methyl-2-p-chlorophenylbutyronitrile |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0045088B1 (en, 2012) |
| JP (1) | JPS5753450A (en, 2012) |
| KR (1) | KR830006190A (en, 2012) |
| AT (1) | ATE8043T1 (en, 2012) |
| BR (1) | BR8104832A (en, 2012) |
| CS (1) | CS226031B2 (en, 2012) |
| DD (1) | DD201674A5 (en, 2012) |
| DE (1) | DE3164308D1 (en, 2012) |
| DK (1) | DK301981A (en, 2012) |
| IL (1) | IL63427A (en, 2012) |
| PL (1) | PL129368B1 (en, 2012) |
| ZA (1) | ZA815132B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100598271B1 (ko) * | 1999-12-20 | 2006-07-07 | 에스케이 주식회사 | 3-(1-시아노알킬)벤조산의 제조방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5325538A (en) * | 1976-08-23 | 1978-03-09 | Sumitomo Chem Co Ltd | Preparation of 3-methyl-2-(4-halogenophenyl)butyronitril |
-
1981
- 1981-07-08 DK DK301981A patent/DK301981A/da not_active Application Discontinuation
- 1981-07-24 KR KR1019810002692A patent/KR830006190A/ko not_active Ceased
- 1981-07-24 CS CS815676A patent/CS226031B2/cs unknown
- 1981-07-24 JP JP56115417A patent/JPS5753450A/ja active Pending
- 1981-07-27 EP EP81105930A patent/EP0045088B1/en not_active Expired
- 1981-07-27 ZA ZA815132A patent/ZA815132B/xx unknown
- 1981-07-27 AT AT81105930T patent/ATE8043T1/de not_active IP Right Cessation
- 1981-07-27 DE DE8181105930T patent/DE3164308D1/de not_active Expired
- 1981-07-27 DD DD81232127A patent/DD201674A5/de unknown
- 1981-07-27 BR BR8104832A patent/BR8104832A/pt unknown
- 1981-07-27 IL IL63427A patent/IL63427A/xx unknown
- 1981-07-28 PL PL1981232390A patent/PL129368B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK301981A (da) | 1982-01-29 |
| PL129368B1 (en) | 1984-05-31 |
| EP0045088B1 (en) | 1984-06-20 |
| PL232390A1 (en, 2012) | 1982-02-15 |
| IL63427A0 (en) | 1981-10-30 |
| KR830006190A (ko) | 1983-09-20 |
| BR8104832A (pt) | 1982-04-13 |
| JPS5753450A (en) | 1982-03-30 |
| ZA815132B (en) | 1982-10-27 |
| EP0045088A1 (en) | 1982-02-03 |
| ATE8043T1 (de) | 1984-07-15 |
| DD201674A5 (de) | 1983-08-03 |
| DE3164308D1 (en) | 1984-07-26 |
| IL63427A (en) | 1985-02-28 |
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