Ethanol → Ethyl 4-iodobenzoate

HRID 1440497Notes

Reaction equation

HRID 1440497 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11](O)[CH3:12].S(=O)(=O)(O)O>>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:11][CH3:12])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 120854-Iodobenzoic acid

Product 1

HCID 142891Ethyl 4-iodobenzoate

Procedure

To a suspension of 24.9 g (100.4 mmol) of 4-iodobenzoic acid in 46.25 g (58.9 ml, 1.0 mol) of ethanol (100%) was added 3.0 ml of conc. sulfuric acid. The resulting mixture was refluxed for 60 minutes, and then distilled until a clear, homogeneous solution was obtained. The solution was allowed to cool to room temperature, partitioned between 250 ml of water and 250 ml of pentane, and the layers were separated. The aqueous phase was washed with 3×100 ml-portions of pentane. All organic phases were combined, washed with brine solution, dried over MgSO4, filtered and concentrated in vacuo to a dark yellow oil. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) yielded the title compound as a clear, light yellow oil. PMR (CDCl3): d 1.39 (3H, t, J=7.2 Hz), 4.37 (2H, q, J=7.2 Hz), 7.73-7.82 (4H, m).

Workup

  1. temperatureThe resulting mixture was refluxed for 60 minutes
  2. distillationdistilled until a clear, homogeneous solution
  3. customwas obtained
  4. custompartitioned between 250 ml of water and 250 ml of pentane
  5. customthe layers were separated
  6. washThe aqueous phase was washed with 3×100 ml-portions of pentane
  7. washwashed with brine solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo to a dark yellow oil
  11. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-eb526f818c2244e88c7911e2d53aea39
Source dataset
uspto-grants-1996_03
Patent number
US05498795

Reaction notes

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