JPS58208262A - ２−（ｅ）−フエニルメチレンシクロヘプタン−１−オン−（ｅ）−オキシムの製造方法 - Google Patents
２−（ｅ）−フエニルメチレンシクロヘプタン−１−オン−（ｅ）−オキシムの製造方法Info
- Publication number
- JPS58208262A JPS58208262A JP58056809A JP5680983A JPS58208262A JP S58208262 A JPS58208262 A JP S58208262A JP 58056809 A JP58056809 A JP 58056809A JP 5680983 A JP5680983 A JP 5680983A JP S58208262 A JPS58208262 A JP S58208262A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- water
- alcohol
- phenylmethylenecycloheptan
- mol
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 150000002443 hydroxylamines Chemical class 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 150000007824 aliphatic compounds Chemical class 0.000 claims 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 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 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- -1 aliphatic alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU2251/997/82 | 1982-04-01 | ||
| HU82997A HU185518B (en) | 1982-04-01 | 1982-04-01 | Process for preparing 2-/e/-phenyl-methylene-cycloheptan-1-one-/e/-oxime |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58208262A true JPS58208262A (ja) | 1983-12-03 |
Family
ID=10952372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58056809A Pending JPS58208262A (ja) | 1982-04-01 | 1983-03-31 | ２−（ｅ）−フエニルメチレンシクロヘプタン−１−オン−（ｅ）−オキシムの製造方法 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS58208262A (xx) |
| AT (1) | AT384423B (xx) |
| BE (1) | BE896279A (xx) |
| CA (1) | CA1210027A (xx) |
| CH (1) | CH656121B (xx) |
| DD (1) | DD209619A5 (xx) |
| DE (1) | DE3311895A1 (xx) |
| DK (1) | DK148783A (xx) |
| ES (1) | ES521096A0 (xx) |
| FI (1) | FI831087L (xx) |
| FR (1) | FR2524464B1 (xx) |
| GB (1) | GB2117773B (xx) |
| HU (1) | HU185518B (xx) |
| IL (1) | IL68079A (xx) |
| IT (1) | IT1194184B (xx) |
| NL (1) | NL8301175A (xx) |
| SE (1) | SE8301817L (xx) |
| YU (1) | YU77683A (xx) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4083978A (en) * | 1976-01-27 | 1978-04-11 | Egyt Gyogyszervegyeszeti Gyar | Oxime ethers |
-
1982
- 1982-04-01 HU HU82997A patent/HU185518B/hu not_active IP Right Cessation
-
1983
- 1983-03-07 IL IL68079A patent/IL68079A/xx unknown
- 1983-03-28 BE BE1/10748A patent/BE896279A/fr not_active IP Right Cessation
- 1983-03-29 ES ES521096A patent/ES521096A0/es active Granted
- 1983-03-30 SE SE8301817A patent/SE8301817L/xx not_active Application Discontinuation
- 1983-03-30 FI FI831087A patent/FI831087L/fi not_active Application Discontinuation
- 1983-03-30 DK DK148783A patent/DK148783A/da not_active IP Right Cessation
- 1983-03-31 GB GB08308956A patent/GB2117773B/en not_active Expired
- 1983-03-31 JP JP58056809A patent/JPS58208262A/ja active Pending
- 1983-03-31 CH CH179183A patent/CH656121B/de unknown
- 1983-03-31 CA CA000425105A patent/CA1210027A/en not_active Expired
- 1983-03-31 DE DE19833311895 patent/DE3311895A1/de not_active Withdrawn
- 1983-03-31 FR FR8305314A patent/FR2524464B1/fr not_active Expired
- 1983-04-01 AT AT0116983A patent/AT384423B/de not_active IP Right Cessation
- 1983-04-01 IT IT20428/83A patent/IT1194184B/it active
- 1983-04-01 NL NL8301175A patent/NL8301175A/nl not_active Application Discontinuation
- 1983-04-01 YU YU00776/83A patent/YU77683A/xx unknown
- 1983-04-04 DD DD83249465A patent/DD209619A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1194184B (it) | 1988-09-14 |
| NL8301175A (nl) | 1983-11-01 |
| DD209619A5 (de) | 1984-05-16 |
| IT8320428A1 (it) | 1984-10-01 |
| IL68079A (en) | 1986-10-31 |
| ES8405366A1 (es) | 1984-06-01 |
| ES521096A0 (es) | 1984-06-01 |
| FR2524464B1 (fr) | 1986-05-30 |
| SE8301817L (sv) | 1983-10-02 |
| ATA116983A (de) | 1987-04-15 |
| IT8320428A0 (it) | 1983-04-01 |
| GB8308956D0 (en) | 1983-05-11 |
| AT384423B (de) | 1987-11-10 |
| CH656121B (xx) | 1986-06-13 |
| HU185518B (en) | 1985-02-28 |
| BE896279A (fr) | 1983-09-28 |
| CA1210027A (en) | 1986-08-19 |
| FR2524464A1 (fr) | 1983-10-07 |
| YU77683A (en) | 1985-12-31 |
| IL68079A0 (en) | 1983-06-15 |
| SE8301817D0 (sv) | 1983-03-30 |
| DE3311895A1 (de) | 1983-10-06 |
| FI831087L (fi) | 1983-10-02 |
| GB2117773A (en) | 1983-10-19 |
| DK148783A (da) | 1983-10-02 |
| GB2117773B (en) | 1985-08-29 |
| DK148783D0 (da) | 1983-03-30 |
| FI831087A0 (fi) | 1983-03-30 |
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