Ethanol → Ethyl 4-iodobenzoate

HRID 129606Notes

Reaction equation

HRID 129606 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:15](O)[CH3:16]>>[CH2:15]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=1)[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 120854-Iodobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 142891Ethyl 4-iodobenzoate

Procedure

To a suspension of 10 g (40.32 mmol) of 4-iodobenzoic acid in 100 ml absolute ethanol was added 2 ml thionyl chloride and the mixture was then heated at reflux for 3 hours. Solvent was removed in vacuo and the residue was dissolved in 100 ml ether. The ether solution was washed with saturated NaHCO3 and saturated NaCl solutions and dried (MgSO4). Solvent was then removed in vacuo and the residue kugelrohr distilled (100 degrees C.; 0.55 mm) to give the title compound as a colorless oil, PMR (CDCl3): δ1.42 (3H, t, J~7 Hz), 4,4 (2H, q, J~7 Hz), 7.8 (4H).

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 3 hours
  3. customSolvent was removed in vacuo
  4. dissolutionthe residue was dissolved in 100 ml ether
  5. washThe ether solution was washed with saturated NaHCO3 and saturated NaCl solutions
  6. dry with materialdried (MgSO4)
  7. customSolvent was then removed in vacuo
  8. distillationthe residue kugelrohr distilled (100 degrees C.; 0.55 mm)

Sources & evidence

ORD record
ord-57c8f33c325b476489458a0c64276280
Source dataset
uspto-grants-1995_11
Patent number
US05468879

Reaction notes

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