tags
vanillinsodium thiosulfateethanoliodine

video tutorial 5-Iodovanillin preparation from vanillin

  • Goal: synthesize 5-iodovanillin by iodination of vanillin.
  • Reagents: vanillin, potassium iodide, sodium bicarbonate, iodine; solvent: water.
  • Process: dissolve KI and bicarbonate in water, suspend vanillin, add iodine gradually to form I3-; stir ~2 hours until color changes (yellow to orange) and a yellow solid forms.
  • Workup: vacuum filter, wash with dilute sodium thiosulfate solution followed by cold water; dry; seal in calcium chloride to complete drying.
  • Purification: recrystallize from a boiling 20% ethanol / 80% isopropyl alcohol mixture; yield is nearly quantitative; crystals are pale tan to almost gold.
  • Product notes: faint vanillin aroma; useful intermediate for 5-hydroxyvanillin and syringaldehyde.

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