Sodium Iodide → 5-Ethyl-2-hydroxy-3-iodo-benzaldehyde

HRID 1066638Notes

Reaction equation

HRID 1066638 reaction equation
[CH2:1]([C:3]1[CH:10]=[C:7]([CH:8]=[O:9])[C:6]([OH:11])=[CH:5][CH:4]=1)[CH3:2].[I-:12].[Na+].ClN>CN(C=O)C>[CH2:1]([C:3]1[CH:4]=[C:5]([I:12])[C:6]([OH:11])=[C:7]([CH:10]=1)[CH:8]=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 25423MonochloramineHCID 64298115-Ethyl-2-hydroxybenzaldehyde

Product 1

HCID 220399725-Ethyl-2-hydroxy-3-iodo-benzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 30.0 g of 5-ethyl-salicylaldehyde (Reg.No. 52411-35-5) in 500 ml of DMF was treated with 36.0 g of sodium iodide and 67.6 g of Chloroamine T and stirred for one hour at room temperature. The reaction mixture was concentrated in a high vacuum, poured into ice-water, made acid with 2N hydrochloric acid and extracted with ethyl acetate. The organic phases were washed with aqueous sodium thiosulphate solution, saturated sodium chloride solution and ice-water, dried over sodium sulphate and concentrated. The residue was taken up in ether-hexane (1:1) and filtered. The filtrate was concentrated and gave 45.8 g of 5-ethyl-2-hydroxy-3-iodo-benzaldehyde; MS (EI) m/z 276 M+.

Workup

  1. concentrationThe reaction mixture was concentrated in a high vacuum
  2. additionpoured into ice-water
  3. extractionextracted with ethyl acetate
  4. washThe organic phases were washed with aqueous sodium thiosulphate solution, saturated sodium chloride solution and ice-water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-21ed42104e4b42269246f59114e84ef3
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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