5-Iodo-1,2,3-trimethoxybenzene → 4-Iodo-2,6-dimethoxyphenol

HRID 984174Notes

Reaction equation

HRID 984174 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10]C)=[C:6]([O:8][CH3:9])[CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([I:1])[CH:3]=[C:4]([O:12][CH3:13])[C:5]=1[OH:10]

Participants

4

Reactant 2

HCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 224855374-Iodo-2,6-dimethoxyphenol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-iodo-1,2,3-trimethoxybenzene (3.2 g) in 1,2-dichloroethane (40 mL) was added aluminum chloride (1.6 g). The mixture was stirred at 60° C. for 4 hours and evaporated. The residue was dissolved in 1 M aqueous sodium hydroxide solution and washed with ether. The aqueous layer was then acidified and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated to give the title compound as white crystalline powder.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in 1 M aqueous sodium hydroxide solution
  3. washwashed with ether
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-4fca9f91574e497290c85d06dbaccbac
Source dataset
uspto-grants-2005_03
Patent number
US06867221B2

Reaction notes

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