Methyl iodide → 4-Iodo-2-methoxybenzyl alcohol

HRID 1421696Notes

Reaction equation

HRID 1421696 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[C:11]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C>[CH3:11][O:1][C:2]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 187797342-(Hydroxymethyl)-5-iodophenol

Product 1

HCID 187797924-Iodo-2-methoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-4-iodo-benzylalcohol from Step 3 (1.0 g, 4.0 mmol), Cs2CO3 (1.3 g, 4.0 mmol) and iodomethane (0.25 mL, 4.0 mmol) were dissolved in DMF and heated to 80° for 1 hour and then stirred at room temperature for 2 hours. The DMF was removed in vacuo and the residue was partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc (2×). The organic layers were combined, washed with H2O and brine, dried (MgSO4), filtered and concentrated to yield an oil. This oil was purified by flash chromatography eluting product with 30% EtOAC/Hexane to give the title compound.

Workup

  1. temperatureheated to 80° for 1 hour
  2. customThe DMF was removed in vacuo
  3. customthe residue was partitioned between H2O and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc (2×)
  5. washwashed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield an oil
  10. customThis oil was purified by flash chromatography
  11. washeluting product with 30% EtOAC/Hexane

Sources & evidence

ORD record
ord-b83e0f681e2748e286146465b4abbc59
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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