FIELD: organic synthesis.
SUBSTANCE: invention relates to a novel method fir preparing trans-3,4-dialkylcyclopentan-1-ols having general formula 1:
(1),
where R represents n-butyl, n-hexyl, or n-octyl, which can find use in fine organic synthesis, production of lacquer materials, high-efficiency antiscoring and antiwear additives for lubricating oils, and biologically active substances. Method is characterized by that α-olefins having general formula RCH=CH2 (R as above) are brought into reaction with ethylaluminum dichloride EtAlCl2 and magnesium at molar ratio 10:(5-7):(5-7), respectively, in presence of zirconacene dichloride Cp2ZrCl2 as catalyst at molar ratio of the latter to α-olefin 0.03-0.07 under argon atmosphere, at room temperature and atmospheric pressure in tetrahydrofuran medium, after which nickel chloride phosphine complex [NiCl2·2Ph3P] is added at molar ratio to α-olefin 0.08-0.12 and methyl formate in amount trice as great as that of EtAlCl2. Yield of desired product is 54-72%.
EFFECT: optimized synthesis conditions.
1 tbl, 13 ex
Title | Year | Author | Number |
---|---|---|---|
METHOD FOR PRODUCTION OF 1,3,4-TRIALKYLCYCLOPENTANE-1-OLS | 2003 |
|
RU2250892C2 |
METHOD FOR PRODUCTION OF 3-n-ALKYL-1-HYDROXYCYCLOPENTANE-n-ALKYLCARBOXYLATES | 2004 |
|
RU2307825C2 |
OPTICALLY ACTIVE 3-ALKYL-1-HYDROXY-1'S-METHYLCYCLOPENTANOL SYNTHESIS METHOD | 2008 |
|
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|
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SPIRO[3,4]OCTAN-6-OL SYNTHESIS METHOD | 2007 |
|
RU2378245C2 |
METHOD FOR COMBINED SYNTHESIS OF 1-ETHYL-2-ALKYLIDENEALUMINACYCLOPENTANES AND 1-ETHYL-2-METHYLENE-3-ALKYLALUMINACYCLOPENTANES | 2009 |
|
RU2423370C2 |
METHOD OF PREPARING 1-VINYL-1-METHYL-3-ALKYLSILACYCLOPENTANES | 2000 |
|
RU2173320C1 |
METHOD OF PREPARING 1-ALKOXY-3-ALKYLALUMACYCLPENTANES | 1998 |
|
RU2139877C1 |
METHOD OF PRODUCING 9-ETHYL-11-ALKYL-9-ALUMINABICYCLO[6,3,0]UNDEC-1(8)-ENES | 2008 |
|
RU2373214C1 |
METHOD OF PRODUCING 2-ALKYL-1,4-BIS(DIETHYLALUMINIO)BUTANES | 2010 |
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RU2459828C2 |
Authors
Dates
2005-03-10—Published
2003-05-19—Filed