FIELD: chemistry.
SUBSTANCE: invention concerns organic chemistry, particularly method of obtaining spiro[3,4]oct-6-ylformiate. Method  (1) involves interaction of methylenecyclobutane with triethylaluminium (AlEt3) in the presence of zirconocene dichloride catalyst (Cp2ZrCl2) at molar ratio of methylenecyclobutane: AlEt3:Cp2ZrCl2=10:(11-15):(0.5-0.7) in argon atmosphere at room temperature and atmospheric pressure in hexane for 7 hours, with further addition of copper chloride catalyst (CuCl) in amount equimolar to Cp2ZrCl2, and alkylformiate of the general formula HCO2R (where R=Et, n-Pr, n-Bu) thrice exceeding amount of AlEt3, to reaction mass at -15°C, further stirring at room temperature for 8-10 hours, and acid hydrolysis of reaction mass. Total output of end product after acid hydrolysis of reaction mass reaches 73-89%.
 (1) involves interaction of methylenecyclobutane with triethylaluminium (AlEt3) in the presence of zirconocene dichloride catalyst (Cp2ZrCl2) at molar ratio of methylenecyclobutane: AlEt3:Cp2ZrCl2=10:(11-15):(0.5-0.7) in argon atmosphere at room temperature and atmospheric pressure in hexane for 7 hours, with further addition of copper chloride catalyst (CuCl) in amount equimolar to Cp2ZrCl2, and alkylformiate of the general formula HCO2R (where R=Et, n-Pr, n-Bu) thrice exceeding amount of AlEt3, to reaction mass at -15°C, further stirring at room temperature for 8-10 hours, and acid hydrolysis of reaction mass. Total output of end product after acid hydrolysis of reaction mass reaches 73-89%.
EFFECT: possible application in fine organic synthesis and production of paint coating materials and bioactive substances.
1 ex, 1 tbl
| Title | Year | Author | Number | 
|---|---|---|---|
| SPIRO[3,4]OCTAN-6-OL SYNTHESIS METHOD | 2007 | 
 | RU2378245C2 | 
| METHOD OF 6-HYDROXYSPIRO[3,4]OCTANE-6-ALKYLCARBOXYLATES OBTAINMENT | 2007 | 
 | RU2355677C1 | 
| METHOD OF OBTAINING 6-THIASPIRO[3,4]OCTANE | 2007 | 
 | RU2368606C2 | 
| OPTICALLY ACTIVE 3-ALKYL-1-HYDROXY-1'S-METHYLCYCLOPENTANOL SYNTHESIS METHOD | 2008 | 
 | RU2400466C2 | 
| METHOD FOR PRODUCTION OF 3-n-ALKYL-1-HYDROXYCYCLOPENTANE-n-ALKYLCARBOXYLATES | 2004 | 
 | RU2307825C2 | 
| METHOD FOR PREPARING 1-(3',3'-DIALKOXYPROP-1'-YL)-2-HYDRO[60]FULLERENES | 2003 | 
 | RU2238930C1 | 
| METHOD OF 6-ETHYL-6-ALUMINASPIRO[3,4] OCTANE | 2007 | 
 | RU2342392C2 | 
| METHOD OF SPIRO[3,3]HEPTANE PRODUCTION | 2007 | 
 | RU2350595C1 | 
| METHOD OF PRODUCING exo-TRICYCLO[4,2,1,0]NONANE-3-SPIRO-1'-(3'-SELENIUM)CYCLOPENTANE | 2008 | 
 | RU2408599C2 | 
| METHOD OF PRODUCING exo-TRICYCLO[4,2,1,0]NONANE-3-SPIRO-1'-(3'-THIA)CYCLOPENTANE | 2008 | 
 | RU2408590C2 | 
Authors
Dates
2009-05-20—Published
2007-07-09—Filed