Ethanol → Ethyl 4-iodobenzoate
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
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
- temperaturethe mixture was then heated
- temperatureat reflux for 3 hours
- customSolvent was removed in vacuo
- dissolutionthe residue was dissolved in 100 ml ether
- washThe ether solution was washed with saturated NaHCO3 and saturated NaCl solutions
- dry with materialdried (MgSO4)
- customSolvent was then removed in vacuo
- distillationthe residue kugelrohr distilled (100 degrees C.; 0.55 mm)
Sources & evidence
- ORD record
- ord-6724f220dc7c4e89ac64b79ac6a33d74
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05723620
Reaction notes
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