S(=O)(=O)(O)O.Br[C:7]12[CH2:14][CH2:13][C:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])([CH2:11][CH2:12]1)[CH2:9][CH2:8]2.[CH:20]([OH:22])=[O:21]>S([O-])([O-])(=O)=O.[Ag+2]>[CH2:15]([C:10]12[CH2:13][CH2:14][C:7]([C:20]([OH:22])=[O:21])([CH2:12][CH2:11]1)[CH2:8][CH2:9]2)[CH2:16][CH2:17][CH2:18][CH3:19]In another flask, 150 ml of concentrated sulfuric acid and 1.3 g of silver sulfate (Ag2SO4) were mixed and cooled to 5° C., and 5 ml of a solutoin of 3 g of the aforesaid 1-bromo-4-pentylbicyclo(2,2,2)octane in n--C6H14 was added. Subsequently, 1 ml of 98% HCOOH was gradually added thereto. After the evolution of gas ceased, the reaction solution was added to 600 ml of ice water to deposit crystals. The crystals were collected by filtration to obtain 4-pentylbicyclo[2,2,2]octanecarboxylic acid.
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