SU270724A1 - METHOD OF OBTAINING SIMPLE AIRS ALCOHOLIC SERIES ALCOHOLS - Google Patents
METHOD OF OBTAINING SIMPLE AIRS ALCOHOLIC SERIES ALCOHOLSInfo
- Publication number
- SU270724A1 SU270724A1 SU1323007A SU1323007A SU270724A1 SU 270724 A1 SU270724 A1 SU 270724A1 SU 1323007 A SU1323007 A SU 1323007A SU 1323007 A SU1323007 A SU 1323007A SU 270724 A1 SU270724 A1 SU 270724A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- airs
- obtaining simple
- series alcohols
- alcoholic
- mol
- Prior art date
Links
- 150000001298 alcohols Chemical class 0.000 title description 2
- 230000001476 alcoholic Effects 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 210000004369 Blood Anatomy 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N Propargyl alcohol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 102100000047 SCAMP3 Human genes 0.000 description 1
- 101710029433 SCAMP3 Proteins 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000004936 stimulating Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Description
Изобретение относитс к способу получени не описанных в литературе простых эфиров первичных или вторичных спиртов ацетиленового р да. Полученные эфиры содержат в своем составе реакционный центр в виде тройной св зи и могут найти применение как мономеры и физиологически активные вещества.This invention relates to a process for the preparation of primary or secondary alcohols of the acetylene series not described in the literature. The resulting esters contain a triple bond in the reaction center and can be used as monomers and physiologically active substances.
Так, эти соединени , име низкую токсичность , вл ютс сильными препаратами, оказывающими стимулирующее действие на кроветворение .Thus, these compounds, having low toxicity, are powerful drugs that have a stimulating effect on blood formation.
Предложенный способ состоит в том, что первичные или вторичные ацетиленовые спирты , например лропаргиловый, обрабатывают моногалоидными алкилами в жидком аммиаке в присутствии амида натри при температуре от -35 до -40°С. Выход целевого продукта около 80 %.The proposed method consists in the fact that primary or secondary acetylenic alcohols, for example, lropargyl, are treated with monohalide alkyls in liquid ammonia in the presence of sodium amide at a temperature of from -35 to -40 ° C. The yield of the target product is about 80%.
Пример 1. Получение децилокси-3-пропина-1 . В 500 мл жидкого аммиака, охлажденного до температуры от -35 до -40°С смесью ацетона с сухим льдом, добавл ют при непрерывном перемещивании 0,2-0,3 г нитрата железа и 7,59 г (0,33 моль) металлического натри . После перемещивани 1 час к реакционной смеси прикапывают 16,8 г (0,3 моль) пропаргилового спирта в 50 мл абсолютного эфира и перемещивание продолжают 3 час. Затем в реакционную смесь прикапываютExample 1. Getting decyloxy-3-propyne-1. In 500 ml of liquid ammonia, cooled to a temperature of -35 to -40 ° C with a mixture of acetone and dry ice, 0.2-0.3 g of iron nitrate and 7.59 g (0.33 mol) of metallic on three . After moving 1 hour to the reaction mixture, 16.8 g (0.3 mol) of propargyl alcohol in 50 ml of absolute ether are added dropwise and the transfer is continued for 3 hours. Then the reaction mixture is added dropwise.
44,2 г (0,2 моль) децилового бромида и перемешивание продолжают 12 /йс. Аммиак испар ют , к остатку добавл ют 100 мл воды и 150- 200 J/л серного эфира, воднощелочной раствор экстрагируют серным эфиром. Объединенные эфирные выт жки нейтрализуют 50%-ной HCI, отмывают водой до нейтральной реакции и сушат прокаленным .MgSO. После отгонки эфира продукт разгон ют в вакууме. Выделено 30,7 г (78,05%) децилокси-З-пропина-1; т. кип. 133-135°С (5 мм рт. ст.); 1,4425; df 0,8348, MRo вычислено 61,875, MRo найдено 61.871.44.2 g (0.2 mol) of decyl bromide and stirring are continued 12 / ic. The ammonia is evaporated, 100 ml of water and 150-200 J / l of sulfuric ether are added to the residue, the aqueous alkaline solution is extracted with sulfuric ether. The combined ether extracts are neutralized with 50% HCI, washed with water until neutral, and dried with calcined. MgSO4. After distilling off the ether, the product is dispersed in vacuo. 30.7 g (78.05%) of decyloxy-3-propyne-1 was isolated; m.p. 133-135 ° С (5 mm of mercury); 1.4425; df 0.8348, MRo calculated 61.875, MRo found 61.871.
Найдено, %: С 79,38; П 12,53; 12,27.Found,%: C 79.38; P 12.53; 12.27.
С|зП24О.S | zP24O.
Вычислено, %: С 79,58; Н 12,24.Calculated,%: C 79.58; H 12.24.
Пример 2. Синтез децилокси-З-гептина-1. В 500 мл жидкого аммиака, охлажденного до температуры от -35 до -40°С смесью ацетона с сухим льдом, добавл ют 0,2-0,3 г нитрата железа и 7,5 г (0,3 моль) металлического натри . Смесь перемешивают 2 час н добавл ют 31,4 г (0,3 моль) гексин-1-ола-З в 50 мл абсолютного эфира и перемещивание продолжают 3 час, после чего прикапывают 44,2 г (0,2 моль) децилового бромида. Перемещивапие продолжают 20 час. Аммиак испар ют, остаток обрабатывают как в примере 1, 3 Выделено 20,5 г (45,75%) децилокси-3-гептаиа-1; т. кип. 128°С (2 мм рт. ст.); п 1,4425; df 0,8280; MRo найдено 76,123, MRo выписпено 75 829 Найдено, %: С 80,73; 80,72; Н 12,87; 12,58. р U Q Вычислено, %: С 80,67, Н 12,605 Чистоту продуктов реакции контролируют тонкослойной хроматографией на силикагеле,ю закреплепном гипсом, в снстеме нетролейный эфир (40-60°) хлороформ (8,5:1,5). Про вителем служит концентрированна H2S04. 4 Предмет изобретени Способ получени простых эфиров сниртов ацетиленового р да, например децилокси-3пропина-1 , отличающийс , что ненасыщенные снирты ацетиленового р да, например пропаргиловый , обрабатывают моногауюидным алкилом , например депиловым оромпдом, в жидком аммиаке в присутствии амида натри при температуре от -35 до -40°С с последующим выделением целевого продукта известными приемами, Example 2. Synthesis of decyloxy-3-heptaine-1. Into 500 ml of liquid ammonia, cooled to a temperature of from -35 to -40 ° C with a mixture of acetone and dry ice, 0.2-0.3 g of iron nitrate and 7.5 g (0.3 mol) of metallic sodium are added. The mixture is stirred for 2 hours and 31.4 g (0.3 mol) of hexin-1-ol-3 is added to 50 ml of absolute ether and the transfer is continued for 3 hours, after which 44.2 g (0.2 mol) of decile bromide are added dropwise. . Moving continues for 20 hours. Ammonia is evaporated, the residue is treated as in Example 1, 3. 20.5 g (45.75%) of decyloxy-3-heptaa-1 are isolated; m.p. 128 ° С (2 mm of mercury); p 1.4425; df 0.8280; MRo found 76,123, MRo discharged 75,829 Found,%: C 80.73; 80.72; H 12.87; 12.58. p U Q Calculated,%: C 80.67, H 12,605 The purity of the reaction products is monitored by thin-layer chromatography on silica gel, fixed gypsum gypsum, in the test system non-trace ether (40-60 °) chloroform (8.5: 1.5). The manufacturer is concentrated H2S04. 4 Subject of the Invention A method for producing ethers of the acetylene row, such as decyloxy-3 propin-1, characterized in that unsaturated acetylene row shots, such as propargyl, are treated with mono-alkyl, such as a depilic orthodromide, in liquid ammonia in the presence of sodium amide at a temperature of - 35 to -40 ° C, followed by separation of the target product by known methods,
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU270724A1 true SU270724A1 (en) |
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