PL240177B1 - 3-methoxybenzaldehyde oxime ethyl ether and method of its preparation - Google Patents
3-methoxybenzaldehyde oxime ethyl ether and method of its preparation Download PDFInfo
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- PL240177B1 PL240177B1 PL432401A PL43240119A PL240177B1 PL 240177 B1 PL240177 B1 PL 240177B1 PL 432401 A PL432401 A PL 432401A PL 43240119 A PL43240119 A PL 43240119A PL 240177 B1 PL240177 B1 PL 240177B1
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- Prior art keywords
- ethyl ether
- methoxybenzaldehyde oxime
- reaction
- preparation
- oxime ethyl
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 16
- VDCBJAPSEUTPTQ-TWGQIWQCSA-N (nz)-n-[(3-methoxyphenyl)methylidene]hydroxylamine Chemical compound COC1=CC=CC(\C=N/O)=C1 VDCBJAPSEUTPTQ-TWGQIWQCSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 3
- 239000002274 desiccant Substances 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000010934 O-alkylation reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000004508 fractional distillation Methods 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical class C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- VDCBJAPSEUTPTQ-UHFFFAOYSA-N n-[(3-methoxyphenyl)methylidene]hydroxylamine Chemical compound COC1=CC=CC(C=NO)=C1 VDCBJAPSEUTPTQ-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest eter etylowy oksymu 3-metoksybenzaldehydu, będący pochodną aromatycznego oksymu 3-metoksybenzaldehydu i posiadający właściwości zapachowe.The present invention relates to 3-methoxybenzaldehyde oxime ethyl ether derived from aromatic 3-methoxybenzaldehyde oxime and having aromatic properties.
Przedmiotem wynalazku jest sposób wytwarzania eteru etylowego oksymu 3-metoksybenzaldehydu.The present invention relates to a process for the preparation of 3-methoxybenzaldehyde oxime ethyl ether.
Eter etylowy oksymu 3-metoksybenzaldehydu, będący aldoksymową pochodną przedstawiono wzorem 1, nie został dotychczas opisany w literaturze.3-methoxybenzaldehyde oxime ethyl ether, which is an aldoxime derivative, is represented by the formula 1, has not been described in the literature so far.
Istotą rozwiązania według wynalazku jest eter etylowy oksymu 3-metoksybenzaldehydu o wzorze 1.The essence of the solution according to the invention is 3-methoxybenzaldehyde oxime ethyl ether of the formula 1.
Istotą rozwiązania według wynalazku jest również sposób wytwarzania eteru etylowego oksymu 3-metoksybenzaldehydu o wzorze 1, polega na tym, że oksym 3-metoksybenzaldehydu poddaje się reakcji O -alkilowania jodoetanem, przy czym reakcję prowadzi się w kolbie na mieszadle magnetycznym w obecności dimetylosulfotlenku jako rozpuszczalnika przez 24 godziny, a po zakończeniu reakcji rozcieńcza się mieszaninę reakcyjną wodą destylowaną i umieszcza całość w rozdzielaczu, następnie mieszaninę ekstrahuje się trzykrotnie heksanem, a połączone warstwy organiczne suszy się bezwodnym siarczanem magnezu, następnie odfiltrowuje się środek suszący i odparowuje rozpuszczalniki, a surowy produkt oczyszcza się za pomocą frakcyjnej destylacji próżniowej.The essence of the solution according to the invention is also the method of producing 3-methoxybenzaldehyde oxime ethyl ether of the formula 1, which consists in subjecting the 3-methoxybenzaldehyde oxime to an O-alkylation reaction with iodoethane, the reaction being carried out in a flask on a magnetic stirrer in the presence of dimethylsulfoxide as a solvent for 24 hours, and after completion of the reaction, the reaction mixture is diluted with distilled water and placed in a separatory funnel, then the mixture is extracted three times with hexane, and the combined organic layers are dried over anhydrous magnesium sulfate, then the drying agent is filtered off and the solvents are evaporated, and the crude product is purified by means of fractional vacuum distillation.
Rozwiązanie według wynalazku jest przedstawione w przykładzie wykonania oraz na schemacie reakcji i określony wzorem 1.The solution according to the invention is shown in the embodiment and in the reaction scheme and is represented by the formula 1.
P r z y k ł a dExample
W kolbie jednoszyjnej, okrągłodennej o pojemności 250 ml umieszczono 5 g (33 mmol) oksymu m-aldehydu anyżowego, 40 ml dimetylosulfotlenku. Kolbę umieszcza się na mieszadle magnetycznym i dodaje małymi porcjami 0,95 g (39,6 mmol) wodorku sodu. Po całkowitym wydzieleniu się wodoru do mieszaniny reakcyjnej wkrapla się 7,72 g (59,08 mmol) jodoetanu. Po upływie 24 h stwierdza się całkowite przereagowanie substratu. Mieszaninę reakcyjną rozcieńcza się około 120 ml wody destylowanej i umieszcza w rozdzielaczu. Mieszaninę reakcyjną trzykrotnie ekstrahuje się 40 ml heksanu. Połączone warstwy organiczne suszy się bezwodnym siarczanem magnezu. Po osuszeniu, odfiltrowuje się środek suszący, a rozpuszczalniki odparowuje na wyparce rotacyjnej. Otrzymuje się 4,5 g surowego produktu. Surowy produkt oczyszcza się za pomocą frakcyjnej destylacji próżniowej, w wyniku której otrzymuje się czysty eter O-etylowy oksymu 3-metoksybenzaIdehydu.5 g (33 mmol) of m-anisaldehyde oxime, 40 ml of dimethylsulfoxide were placed in a 250 ml single necked round bottom flask. The flask is placed on a magnetic stirrer and 0.95 g (39.6 mmol) of sodium hydride is added in small portions. After complete evolution of hydrogen, 7.72 g (59.08 mmol) of iodoethane are added dropwise to the reaction mixture. After 24 h, complete conversion of the substrate is observed. The reaction mixture is diluted with about 120 ml of distilled water and placed in a separating funnel. The reaction mixture is extracted three times with 40 ml of hexane. The combined organic layers are dried over anhydrous magnesium sulfate. After drying, the drying agent is filtered off and the solvents are evaporated on a rotary evaporator. 4.5 g of crude product are obtained. The crude product is purified by fractional vacuum distillation to obtain pure 3-methoxybenzidehyde oxime O-ethyl ether.
Produkt otrzymany według przykładu posiada następujące właściwości fizyczne i spektralne:The product obtained according to the example has the following physical and spectral properties:
1H NMR (400 MHz, CDCI3) δ: 1.32 (t, J=7Hz 3H at C-10); 3.82 (s, 3H at C-8); 4.22 (q, J=7Hz, 2H at C-9); 6.89-6.92 (m, 1H at C-4); 7.10-7.12 (m, 1H at C-5); 7.15-7.16 (m, 1H at C-2); 7.25-7.29 (m, 1H at C-6); 8.03 (s, 1H at C-7) 13C NMR (100 MHz, CDCI3) δ: 14.25 (C-10), 55.42 (C-8), 69.77 (C-9), 110.9 (C-2), 116.0 (C-4). 120.1 (C-5), 129.7 (C-6), 133.2 (C-1), 148.3 (C-7), 159.9 (C-3). 1 H NMR (400 MHz, CDCl 3) δ: 1.32 (t, J = 7 Hz 3 H at C-10); 3.82 (s, 3H at C-8); 4.22 (q, J = 7 Hz, 2H at C-9); 6.89-6.92 (m, 1H at C-4); 7.10-7.12 (m, 1H at C-5); 7.15-7.16 (m, 1H at C-2); 7.25-7.29 (m, 1H at C-6); 8.03 (s, 1H at C-7) 13 C NMR (100 MHz, CDCl3) δ: 14.25 (C-10), 55.42 (C-8), 69.77 (C-9), 110.9 (C-2), 116.0 (C-4). 120.1 (C-5), 129.7 (C-6), 133.2 (C-1), 148.3 (C-7), 159.9 (C-3).
Claims (2)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL432401A PL240177B1 (en) | 2019-12-24 | 2019-12-24 | 3-methoxybenzaldehyde oxime ethyl ether and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL432401A PL240177B1 (en) | 2019-12-24 | 2019-12-24 | 3-methoxybenzaldehyde oxime ethyl ether and method of its preparation |
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| Publication Number | Publication Date |
|---|---|
| PL432401A1 PL432401A1 (en) | 2021-06-28 |
| PL240177B1 true PL240177B1 (en) | 2022-02-28 |
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| PL432401A PL240177B1 (en) | 2019-12-24 | 2019-12-24 | 3-methoxybenzaldehyde oxime ethyl ether and method of its preparation |
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