SU392622A1 - METHOD FOR PRODUCING 2,3-EPOXYHRANE HALENOGENIDES - Google Patents
METHOD FOR PRODUCING 2,3-EPOXYHRANE HALENOGENIDESInfo
- Publication number
- SU392622A1 SU392622A1 SU815229A SU815229A SU392622A1 SU 392622 A1 SU392622 A1 SU 392622A1 SU 815229 A SU815229 A SU 815229A SU 815229 A SU815229 A SU 815229A SU 392622 A1 SU392622 A1 SU 392622A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- producing
- halenogenides
- epoxyhrane
- geranyl
- halide
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 2,3-epoxyhexyl halide Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- JSCUZAYKVZXKQE-JXMROGBWSA-N (2E)-1-bromo-3,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCC\C(C)=C\CBr JSCUZAYKVZXKQE-JXMROGBWSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Chemical group 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
1one
Изобретение относитс к способу получени новых эпоксидированных галоидзамещенных нен1асыщенных алифатических углеводородов, в частности 2,3-э1поксигеранилгалогенида, которые могут найти применение в синтезе биологически активных веществ.This invention relates to a process for the preparation of new epoxidized halosubstituted unsaturated aliphatic hydrocarbons, in particular 2,3-epoxyhexyl halide, which can be used in the synthesis of biologically active substances.
Известно, что геранилбромид используют дл получени фенилгераниловых эфиров.Geranyl bromide is known to be used to prepare phenylheranyl esters.
Эпоксидированные фенилгераниловые эфиры отличны по своим свойствам от последних тем, что они нетоксичны дл теплокровных животных.Epoxidized phenylgeranyl ethers differ in their properties from the latter in that they are non-toxic to warm-blooded animals.
Предложенный способ получени 2,3-эпоксигеранилгалогенидов общей формулыThe proposed method for the preparation of 2,3-epoxy-geranyl halides of the general formula
XX
СНгSNG
NN
RR
RR
где X - атом брома, хлора, иода; R и R - метил или энил,where X is a bromine atom, chlorine, iodine; R and R is methyl or Enil,
заключаетс в том, что геранилгалогенид обшей формулыis that a generalized geranyl halide of the formula
СН.CH.
VyVy
RR
ВAT
где X, R, R имеют вышеуказанные значени , подвергают обработке эпоксидпруюшим агентом , например метахлорнадбензойной кислотой .where X, R, R are as defined above, treated with an epoxy agent, for example, methachloroperbenzoic acid.
В сл1учае использовани вышеуказанного эпоксидирующего агента процесс ведут при 5°С.In the case of using the above epoxidizing agent, the process is carried out at 5 ° C.
Продукт выдел ют известными приемами с выходом до 83,7%.The product is isolated by known methods with a yield of up to 83.7%.
Данное изобретение иллюстрируетс , но не This invention is illustrated, but not
0 ограничиваетс Н ижанриведенным примером.0 is limited to an example.
Пример.Example.
X. Н. X. N.
1 Ч 1 h
5 СН СНь5 CH CH
10,9 г (0,05 моль геранилбромида раствор ют в 100 мл метиленхлорида. При неремешивании при 5°С добавл ют стехиометриче0 ское количество метахлорнадбензойной кислоты в метиленхлориде. После добавлени смесь перемешивают при комнатной температуре в течение ночи. Продукт реакции трилады про5 мывают 10%-ным раствором бикарбоната натри , сушат над безводным сульфатом магни , фильтруют и отгон ют растворитель. Выдел ют 9,8 г (83,7%) соединени ; ng 1,6910. Строение вещества подтверждено ИК и10.9 g (0.05 mol of geranyl bromide is dissolved in 100 ml of methylene chloride. If not stirred at 5 ° C, a stoichiometric amount of methachloroperbenzoic acid in methylene chloride is added. After the addition, the mixture is stirred at room temperature overnight. The reaction product is washed with trilade 10 % sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off. 9.8 g (83.7%) of the compound was isolated; ng 1.6910. The structure of the substance was confirmed by IR and
0 ЯМР-спектроскопией.0 NMR spectroscopy.
33
Предмет и з о б р с т с п и Subject and s about br with t with p and
Способ получени 2,3-эпоксигеранилгалогенидов общей формулыThe method of producing 2,3-epoxyhexyl halides of the general formula
СНтSNT
RR
RR
где X - атом брома, хлора, иода, R и R метил или этил,where X is a bromine atom, chlorine, iodine, R and R methyl or ethyl,
отличающийс тбм, что гераниЛГалогенид общей формулыcharacterized by tbm, that geranyl is a halide of the general formula
СНзSNS
Е E
RR
где X, R, R имеют вышеуказавиые значеии , подвергают взаимодействию с зпоксидирующим агентом, иапример с метахло-рвадбензойиой кислотой, с последующим выделением продукта известными приемами.where X, R, R have the above meanings, are reacted with a zpoxidising agent, for example, with methachloromethane, followed by isolation of the product by known methods.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU392622A1 true SU392622A1 (en) |
Family
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