Iodine → 1,3,5-Trimethoxy-4-iodobenzene

HRID 919184Notes

Reaction equation

HRID 919184 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[CH:4]=1.[I:13](O)(=O)=O.II>C(O)C>[I:13][C:4]1[C:5]([O:11][CH3:12])=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 693011,3,5-Trimethoxybenzene

Product 1

HCID 122540971,3,5-Trimethoxy-4-iodobenzeneYield 171.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

1,3,5-Trimethoxybenzene (14.5 g, 0.086 mol) was dissolved in 10 mL of ethanol at rt before warming to 50° C. in a waterbath after which, an aqueous solution of iodic acid (7.6 g, 0.043 mol) was added. Solid iodine (21.88 g, 0.086 mol) was dissolved in 20 mL of ethanol and the resultant solution was added portion-wise over 60 min to the reaction mixture. Stirring was continued at 50° C. until the color of I faded and a white precipitate appeared. The reaction mixture2 was stirred at room temperature for 18 h. The precipitate that formed was isolated via vacuum filtration, washed with ethanol and crystallized from methanol to yield 6 (21.7 g, 86%) as white crystals.

Workup

  1. customwas continued at 50° C. until the color of I
  2. stirringThe reaction mixture2 was stirred at room temperature for 18 h
  3. customThe precipitate that formed
  4. customwas isolated via vacuum filtration
  5. washwashed with ethanol
  6. customcrystallized from methanol

Sources & evidence

ORD record
ord-b6e4dd6f4d394baebd2d549d931e414f
Source dataset
uspto-grants-2016_03
Patent number
US09273021B2

Reaction notes

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