SU215961A1 - The method of obtaining substituted in the Dreu vinylaryl ethers - Google Patents
The method of obtaining substituted in the Dreu vinylaryl ethersInfo
- Publication number
- SU215961A1 SU215961A1 SU1025629A SU1025629A SU215961A1 SU 215961 A1 SU215961 A1 SU 215961A1 SU 1025629 A SU1025629 A SU 1025629A SU 1025629 A SU1025629 A SU 1025629A SU 215961 A1 SU215961 A1 SU 215961A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dreu
- obtaining substituted
- vinylaryl
- ethers
- ether
- Prior art date
Links
- 150000002170 ethers Chemical class 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000002194 synthesizing Effects 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- -1 p-vinyloxyphenylmethyl carbinol Chemical compound 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-Dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229920001567 Vinyl ester Polymers 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002734 organomagnesium group Chemical group 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000006886 vinylation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Description
Данное изобретение относитс к области получени замещенных в дре винилариловых эфиров, которые могут найти применение в качестве сырь дл получени ионообменных смол и сшивающих реагентов.This invention relates to the field of producing vinyl-aryl esters substituted in wood, which can be used as a raw material for the preparation of ion exchange resins and cross-linking reagents.
Предложенный способ вл етс новым и полезным, так как позвол ет получать замещенные в дре винилариловые эфиры, которые трудно нолучить пр мым винилированием .The proposed method is new and useful, since it allows one to obtain vinyl-aryl-substituted esters that are difficult to obtain by direct vinylation.
Предложенный способ состоит в том, что виниловый эфир л-галоид-(хлор или бром)фенола подвергают взаимодействию с магнием в среде органического растворител , например , серного эфира, в присутствии активных галоидных алкилов, например йодистого метила, с последующей обработкой полученного при этом нродукта или углекислотой, или серой, или ацетальдегидом, или окисью этилена, или ацетоном и выделением целевого продукта известным способом.The proposed method consists in the fact that the vinyl ether of l-halo- (chlorine or bromine) phenol is subjected to interaction with magnesium in an environment of an organic solvent, for example, sulfuric ether, in the presence of active halide alkyls, for example methyl iodide, with the subsequent processing of the resulting product or carbon dioxide, or sulfur, or acetaldehyde, or ethylene oxide, or acetone and the selection of the target product in a known manner.
Пример i. Синтез п-винилоксифенилметилкарбинола .Example i. Synthesis of p-vinyloxyphenylmethyl carbinol.
К охлажденному до -20°С раствору п-винилоксифенилбромистого магни , получениему из 9,6 г магни , 39,8 г винилового эфира г-бромфенола и 21,8 г бромистого этила в 500 мл серного эфира, прибавл ют раствор 17,6 г ацетальдегида в 100 лг-г серного эфира и оставл ют смесь при комнатной темиературе на ночь. Продукты реакции разлагают 21 г сухого хлористого аммони , прибавл ют разбавленную (1 :4) сол ную кислоту до растворени осадка. Эфирный раствор отдел ют, промывают водой, 5%-пым раствором соды, сушат потапюм, фильтруют, отгон ют серный эфир и перегон ют остаток в вакууме, прибавив немного бензохинона. Получают 15,1 г (43,30/0 от теории) /1-випилоксифенилмети.л20To a solution of p-vinyloxyphenyl magnesium bromide cooled to -20 ° C, to obtain from 9.6 g of magnesium, 39.8 g of vinyl ether of g-bromophenol and 21.8 g of ethyl bromide in 500 ml of sulfuric ether, add a solution of 17.6 g acetaldehyde in 100 lg-g of sulfuric ether and leave the mixture at room temperature overnight. The reaction products decompose 21 g of dry ammonium chloride, and dilute (1: 4) hydrochloric acid is added to dissolve the precipitate. The ether solution is separated, washed with water, with a 5% soda solution, dried in a shade, filtered, sulfuric ether is distilled off and the residue is distilled in a vacuum, adding a little benzoquinone. 15.1 g are obtained (43.30 / 0 from theory) (1-vipyloxyphenylmethyl. L20)
104-106°С/3 мм, и104-106 ° C / 3 mm, and
кароинола, т. кип. 1.5570; df 1,0742. Caroinol, t. Kip. 1.5570; df 1.0742.
с 74,10; 73.80; П 7,37; 7,49. Найдено,c 74.10; 73.80; P 7.37; 7.49. Found
СюПхаОо.SyuPhaOo.
Вычислено, о/о: С 73,17; Н 7,31. Донолнительно нолучают также 2,25 г (7,7% от теории) /г-в11нилоксистирола. т. кип. 104-108°С/2 лш; ng 1,5452.Calculated, o / o: C 73.17; H 7.31. 2.25 g (7.7% of theory) / g-11 nyloxystyrene are also donated. m.p. 104-108 ° C / 2 lsh; ng 1,5452.
Суммарный выход виниловых эфиров 510/0 от теоретического.The total yield of vinyl esters 510/0 from the theoretical.
Пример 2. Синтез г-винилокситиофенола.Example 2. Synthesis of g-vinyloxythiophenol.
В тщательно просушенный прибор дл магнийорганического синтеза помещают 4,86 г (0,2 г-а) магни , активизированного йодом, 200 мл тетрагидрофурана и медленно прикапывают раствор 15,5 г (0,1 г моль) винилового эфира /г-флорфенола и 18,8 г (0,1 г моль) 1,2-дибромэтана в 100 мл серного эфира; поддержива слабое кипение реакционной смеси (реакцию провод т в атмо4.86 g (0.2 g-a) of magnesium, activated with iodine, 200 ml of tetrahydrofuran are placed in a thoroughly dried organomagnesium synthesis device and a solution of 15.5 g (0.1 g mol) of vinyl ether / g-florphenol and 18.8 g (0.1 g mol) of 1,2-dibromoethane in 100 ml of sulfuric ether; maintaining a weak boiling of the reaction mixture (the reaction is carried out in the atmosphere
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU215961A1 true SU215961A1 (en) | 1968-04-11 |
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