Reaction #1318

Reaction equation

4-iodobenzoic acid

ethanol

thionyl chloride

→

title compound

Ethyl-4-iodobenzoate

Conditions

Workup

1. 1
   Temperaturethe mixture was then heated
2. 2
   Temperatureat reflux for 3 hours
3. 3
   OtherSolvent was removed in vacuo
4. 4
   workup.DISSOLUTIONthe residue was dissolved in 100 ml ether
5. 5
   WashThe ether solution was washed with saturated NaHCO3 and saturated NaCl solutions
6. 6
   Dryingdried (MgSO4)
7. 7
   OtherSolvent was then removed in vacuo
8. 8
   workup.DISTILLATIONthe residue kugelrohr distilled (100 degrees C.; 0.55 mm)

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).

Source