1-Allyl-2,3,4,5-tetramethoxy-6-methylbenzene → 2-(2,3,4,5-Tetramethoxy-6-methylphenyl)acetaldehyde

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Reaction Steps

109 mg of osmium tetroxide were added to a solution of 7.98 of 1-allyl-2,3,4,5-tetramethoxy-6-methylbenzene [prepared as described in step (a) above] in a mixture of 300 ml of dioxane and 100 ml of water, and the resulting mixture was stirred at room temperature for 10 minutes. An aqueous solution of 35.6 g of sodium periodate was then added dropwise, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was freed from the dioxane by evaporation under reduced pressure, and the resulting concentrate was poured into a saturated aqueous solution of sodium chloride, after which it was extracted with diisopropyl ether. The solvent was then removed from the extract by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a gradient elution method with mixtures of hexane and ethyl acetate ranging from 8:1 to 5:1 by volume as the eluent, to give 4.64 g of the title compound.

Provenance & Evidence