Ethanol → Ethyl 4-iodobenzoate

HRID 649338Notes

Reaction equation

HRID 649338 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) 4-iodobenzoic acid (Alfa Products Thiokol/Ventron Division) in 100 ml absolute ethanol was added 2 ml thionyl chloride. This mixture was then heated at reflux for 3 hours. The solvent was removed in vacuo and the residue dissolved in 100ml of 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 distilled on a kugelrohr apparatus (100° C.; 0.55 mm) to give 9 g of title compound as a colorless oil. PMR (CDCl13)δ 1.42 (3H, t, J~7 Hz), 4.4 (2H, q, J~7 Hz), 7.8 (4H, s).

Workup

  1. temperatureThis mixture was then heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in 100ml of 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 distilled on a kugelrohr apparatus (100° C.; 0.55 mm)

Sources & evidence

ORD record
ord-d02c7cdb26bc43b6b212c5e1cc8cdddc
Source dataset
uspto-grants-1988_04
Patent number
US04739098

Reaction notes

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