Iodine → 1-Iodomethyl-4-methyl-2-oxabicyclo[2.2.2]-octan-3-one

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Reaction Steps

7.5 g of iodine was added to a solution of 1.3 g of 1-methyl-4-methylene-1-cyclohexanecarboxylic acid in 50 ml of acetonitrile. The solution was reacted for 3 hours at room temperature. After reaction, 100 ml of an aqueous solution of sodium thiosulfate was added to the reaction solution. The solution was extracted five times with 30 ml of ethyl acetate. The organic layer obtained was washed three times with aqueous sodium thiosulfate solution and two times with an aqueous sodium chloride solution, and was dried over magnesium sulfate. The solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 10 g of silica gel. From the fraction eluted with hexane and ethyl acetate=1:1, the solvent was removed in vacuo, yielding 1.1 g of 1-iodomethyl-4-methyl-2-oxabicyclo[2.2.2]octan-3-one as a pale yellow oil, which had the following physiochemical properties:

Provenance & Evidence