Iodine → 5-Hydroxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Participants

Reaction Steps

3.0 g of 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol (prepared as described in Example 71) were dissolved in a mixture of 40 ml of benzene and 4 ml of pyridine, after which 6.2 g of triphenylphosphine were dissolved in the mixture. After the dissolution, 6.0 g of iodine was added to the solution all at once. The reaction temperatures of the mixture rose to 45° C. The reaction was allowed to continue for another 30 minutes at room temperature, and then the reaction mixture was poured into water and extracted with benzene. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting crude reaction product was subjected to silica gel Lobar column chromatography, and the title compound, melting at 72°-75° C. was obtained from the fraction eluted with benzene.

Provenance & Evidence