CA1088566A - PROCEDE DE PREPARATION DE L'ALCOOL .alpha.-CYANO 3- PHENOXY BENZYLIQUE - Google Patents
PROCEDE DE PREPARATION DE L'ALCOOL .alpha.-CYANO 3- PHENOXY BENZYLIQUEInfo
- Publication number
- CA1088566A CA1088566A CA285,527A CA285527A CA1088566A CA 1088566 A CA1088566 A CA 1088566A CA 285527 A CA285527 A CA 285527A CA 1088566 A CA1088566 A CA 1088566A
- Authority
- CA
- Canada
- Prior art keywords
- metaphenoxy
- benzaldehyde
- anhydrous
- cyano
- mixture
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 20
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 6
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 5
- 239000002609 medium Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 claims description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 5
- -1 3-phenoxy benzyl Chemical group 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229940095076 benzaldehyde Drugs 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000011017 operating method Methods 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 1
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7625938A FR2362829A1 (fr) | 1976-08-27 | 1976-08-27 | Combinaison bisulfitique du metaphenoxy benzaldehyde, procede de preparation et application a la preparation de l'alcool a-cyano 3-phenoxy benzylique |
| FR7625938 | 1976-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1088566A true CA1088566A (fr) | 1980-10-28 |
Family
ID=9177185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA285,527A Expired CA1088566A (fr) | 1976-08-27 | 1977-08-26 | PROCEDE DE PREPARATION DE L'ALCOOL .alpha.-CYANO 3- PHENOXY BENZYLIQUE |
Country Status (11)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA7911B (en) * | 1978-01-31 | 1980-01-30 | Roussel Uclaf | Optically-active substituted benzyl alcohol and process for preparing it |
| FR2458542A1 (fr) * | 1979-06-12 | 1981-01-02 | Roussel Uclaf | Procede de preparation d'alcools a-cyanes optiquement actifs |
| DE2938112A1 (de) * | 1979-09-20 | 1981-04-16 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von (alpha) -cyano-phenoxy-benzyl-estern |
| JPS5970481A (ja) * | 1982-10-14 | 1984-04-20 | Toyota Central Res & Dev Lab Inc | 点溶接方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS515450B1 (enrdf_load_stackoverflow) * | 1971-06-29 | 1976-02-20 |
-
1976
- 1976-08-27 FR FR7625938A patent/FR2362829A1/fr active Granted
-
1977
- 1977-07-26 JP JP8891877A patent/JPS5328142A/ja active Granted
- 1977-08-03 GB GB3259877A patent/GB1567531A/en not_active Expired
- 1977-08-25 IT IT5078577A patent/IT1079949B/it active
- 1977-08-26 CH CH1047077A patent/CH623808A5/fr not_active IP Right Cessation
- 1977-08-26 CA CA285,527A patent/CA1088566A/fr not_active Expired
- 1977-08-26 DK DK378877A patent/DK158303C/da not_active IP Right Cessation
- 1977-08-26 BE BE180440A patent/BE858127A/xx not_active IP Right Cessation
- 1977-08-26 IE IE179077A patent/IE45374B1/en unknown
- 1977-08-26 DE DE19772738643 patent/DE2738643C2/de not_active Expired
- 1977-08-26 NL NL7709435A patent/NL7709435A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK158303B (da) | 1990-04-30 |
| FR2362829B1 (enrdf_load_stackoverflow) | 1979-03-02 |
| NL7709435A (nl) | 1978-03-01 |
| DE2738643C2 (de) | 1986-06-05 |
| BE858127A (fr) | 1978-02-27 |
| DK378877A (da) | 1978-02-28 |
| IE45374L (en) | 1978-02-27 |
| JPS6213342B2 (enrdf_load_stackoverflow) | 1987-03-25 |
| IE45374B1 (en) | 1982-08-11 |
| CH623808A5 (en) | 1981-06-30 |
| IT1079949B (it) | 1985-05-13 |
| FR2362829A1 (fr) | 1978-03-24 |
| DK158303C (da) | 1990-10-01 |
| GB1567531A (en) | 1980-05-14 |
| JPS5328142A (en) | 1978-03-16 |
| DE2738643A1 (de) | 1978-03-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2032988C (fr) | Procede de preparation de derives de la 1-phenyl imidazoline 2,5-dione | |
| EP0566468B1 (fr) | Procédé de préparation d'un dérivé de biphényl | |
| CH632505A5 (fr) | Nouveaux composes a noyau cyclopropanique, procede de preparation et utilisation a la preparation de derives cyclopropaniques a chaine dihalovinylique. | |
| CA1088566A (fr) | PROCEDE DE PREPARATION DE L'ALCOOL .alpha.-CYANO 3- PHENOXY BENZYLIQUE | |
| CH666888A5 (fr) | Procede de dedoublement optique d'un derive de l'acide phenylacetique. | |
| FR2807427A1 (fr) | Plastifiant energetique comprenant un melange eutectique de bis (2,2-dinitropropyl) formal, de 2,2 dinitropropyl- 2,2-dinitrobutylformal et de bis (2,2-dinitrobutyl) formal, et son procede de preparation | |
| CA1265154A (fr) | Procede de preparation des tetrahydro-1,1,2,2 perfluoroalcanols et de leurs esters | |
| EP0001944B1 (fr) | Esters d'alcools alpha-halogénés, procédé de préparation et application à la synthèse d'esters d'alcools alpha-cyanés | |
| CA2319673C (fr) | Procede perfectionne de fabrication d'anhydrides (meth)acryliques mixtes de haute purete | |
| LU83646A1 (fr) | Procede de preparation de derives d'acides cyclopropane carboxyliques porteurs d'une fonction aldehyde | |
| CH411820A (fr) | Procédé de préparation de nouveaux composés hépariniques utilisables, notamment, pour le traitement des troubles de la coagulabilité sanguine | |
| CA2098804C (fr) | Procede de preparation d'un compose steroide delta 9(11) | |
| CA1111447A (fr) | Composes halogenes, procede de preparation et application a la preparation du metaphenoxy benzaldehyde | |
| FR2615852A1 (fr) | Procede pour la preparation et l'isolement de nitriles aromatiques | |
| CA1129886A (fr) | Procede de preparation de n-alcoylamino benzophenones | |
| EP0058591B1 (fr) | Procédé d'épimérisation d'acides trans chrysanthémiques et nouveaux intermédiaires obtenus | |
| EP0166650B1 (fr) | Procédé d'ouverture du cycle des gem dicyanoépoxydes et nouveaux composés obtenus par ce procédé | |
| US4202835A (en) | Preparation of α-cyano-3-phenoxy-benzyl alcohol | |
| EP0034838A2 (fr) | Nouveaux esters halogénoéthyliques d'acide indane acétique, et leur préparation | |
| FR2577926A1 (fr) | Procede de fabrication de la vincamine a partir de la tabersonine | |
| FR2625500A1 (fr) | Perfectionnement a la preparation d'alcools tertiaires et secondaires par l'action d'un compose organo-manganeux sur un compose porteur de groupe carbonyle | |
| BE837804A (fr) | Derives de thiophene ou de furanne et procede pour leur preparation | |
| CH649531A5 (fr) | 1-((2-mercaptocycloalkyl)carbonyl)-l-prolines, leur procede de synthese et compositions pharmaceutiques les contenant. | |
| CH294021A (fr) | Procédé de préparation de 2,6-bis-(5'-benzoylamino-anthraquinonyl-amino-1')-anthraquinone. | |
| CH265052A (fr) | Procédé de préparation de mangano-chlorure d'acétylcholine. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |