SU179766A1 - METHOD OF OBTAINING VINYL ETHER LY-ACETYLAL / INOFENOLS - Google Patents
METHOD OF OBTAINING VINYL ETHER LY-ACETYLAL / INOFENOLSInfo
- Publication number
- SU179766A1 SU179766A1 SU847393A SU847393A SU179766A1 SU 179766 A1 SU179766 A1 SU 179766A1 SU 847393 A SU847393 A SU 847393A SU 847393 A SU847393 A SU 847393A SU 179766 A1 SU179766 A1 SU 179766A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- inofenols
- acetylal
- vinyl ether
- obtaining vinyl
- acetyl
- Prior art date
Links
- QYKIQEUNHZKYBP-UHFFFAOYSA-N vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 title description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229920001567 Vinyl ester Polymers 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ADVGKWPZRIDURE-UHFFFAOYSA-N N-(2-hydroxyphenyl)acetamide Chemical class CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- -1 1-acetyl-p-aminophenol Chemical compound 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Description
Предлагаетс способ получени виниловых эфиров N-ацетиламииофеиолов обработкой последних ацетиленом под давлением 35- 38 атм при температуре . Пропесс ведут в воднодноксановой среде в присутствии едкого калн в качестве катализатора. Эти соединенн могут найти применеиие дл нолучени новых поливиниловых лекарственных пренаратов.A method is proposed for the preparation of vinyl esters of N-acetylami-feiols by treating the latter with acetylene at a pressure of 35-38 atm at a temperature. The process is carried out in a water medium in the presence of a caustic solution as a catalyst. These compounds can be used to obtain new polyvinyl medicinal drugs.
Пример 1. Получение винилового эфира Х-ацетил-/г-аминофенола.Example 1. Preparation of X-acetyl- / g-aminophenol vinyl ester.
В стальной автоклав помещают 20 г N-ацетил-л-аминофепола , 7 г Збо/о-ного едкого кали , 20 г воды и 100 мл диоксана. Ацетилен подают до насыщени им диоксана. Затем реакционную смесь нагревают 30 мин при температуре 180°С. Рабочее давление в автоклаве достигает 35-38 атм.20 g of N-acetyl-l-aminophepol, 7 g of Zbo / normal potassium hydroxide, 20 g of water and 100 ml of dioxane are placed in a steel autoclave. Acetylene is fed until the dioxane is saturated. Then the reaction mixture is heated for 30 minutes at a temperature of 180 ° C. The working pressure in the autoclave reaches 35-38 atm.
Продукт винилировани - коричневую прозрачную жидкость-разгон ют в вакууме , из нее удал ют ко.1ичественно воду и диоксап. Из остатка в колбе noCvie его перекристаллизации из гептана выдел ют виниловый эфир 1 -ацетил-п-аминофенола в виде игл с т. пл. 103°С.The vinylated product — a brown, transparent liquid — is dispersed under vacuum, and quantitatively water and dioxap are removed from it. From the residue in the noCvie flask of its recrystallization from heptane, 1-acetyl-p-aminophenol vinyl ester was isolated in the form of needles with a melting point. 103 ° C.
Найдено в А,: С 67,87; Н 6,32: N 7,95.Found in A: C 67.87; H 6.32: N 7.95.
С,вН„Оо -.C, vN „Oo -.
Вычислено в «Аг. С 67,79; Н 6,21; N 7,90.Calculated in "Ag. C, 67.79; H 6.21; N 7.90.
Строенне пипилового эфира Х-ацетнл-/ь аминофенола доказано гидрированием его в «-фенацетин с т. нл. 136°С (литературные данные; т. нл. 137-138°С).The structure of the acetyl-n-aminophenol pipyl ester is proved by its hydrogenation to α-phenacetin with t. Nl. 136 ° C (literature data; t. Nl. 137-138 ° C).
Пример 2. Получеиие впннлового эфира.Example 2. Poluchenii ester ether.
Процесс ведут аналогнчно примеру 1. Перекристаллнзовывают виниловый эфир N-ацетил-о-аминофеиола из спирта. Выдел ют пластииы с т. нл. 68°С.The process is carried out analogously to example 1. N-acetyl-o-aminopheiol vinyl ether is recrystallized from alcohol. Plastiacia were isolated with m. 68 ° C.
Найдено в о/о: N 8,40.Found in s / a: N 8.40.
C,oHnNOo.C, oHnNOo.
Вычислено в Аь N 7,90.Calculated in Ab N 7.90.
Строение его доказано гидрированием в эти.човый эфир N-апетнл-о-аминофенола.Its structure has been proved by hydrogenation of N-appel-o-aminophenol into this.
Предмет изобретени Subject invention
Способ получени виниловых эфиров Nацетиламинофенолов , отличающийс тем, что N-ацетиламинофенолы обрабатывают ацетиленом под давлением 35-38 атм при температуре 180°С в воднодиоксановой среде в присутствии едкого кали.A method of producing vinyl esters of N acetylaminophenols, characterized in that the N-acetylaminophenols are treated with acetylene under a pressure of 35-38 atm at a temperature of 180 ° C in an aqueous dioxane medium in the presence of potassium hydroxide.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU179766A1 true SU179766A1 (en) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2640808C1 (en) * | 2016-11-30 | 2018-01-12 | Федеральное государственное бюджетное учреждение науки Иркутский институт химии имени А.Е. Фаворского Сибирского отделения Российской академии наук | Method for obtaining vinyl ethers of aminophenols |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2640808C1 (en) * | 2016-11-30 | 2018-01-12 | Федеральное государственное бюджетное учреждение науки Иркутский институт химии имени А.Е. Фаворского Сибирского отделения Российской академии наук | Method for obtaining vinyl ethers of aminophenols |
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