Ethanol → Ethyl 4-iodobenzoate

HRID 1193616Notes

Reaction equation

HRID 1193616 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]>>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:15][CH3:16])=[O:7])=[CH:4][CH:3]=1

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° C.; 0.55 mm) to give the title compound as a colorless oil. PMR (CDCl3): δ 1.42 (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° C.; 0.55 mm)

Sources & evidence

ORD record
ord-b6ce94a1497f46a6a9c6956d613d19cd
Source dataset
uspto-grants-1989_03
Patent number
US04810804

Reaction notes

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