p-Toluenesulfonic acid → Ethyl 3-(2-chloro-4-iodo-phenyl)-3-oxo-propionate

HRID 963399Notes

Reaction equation

HRID 963399 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:3]=1[C:4]([CH:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Cl:1][C:2]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:3]=1[C:4](=[O:5])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19081735Diethyl 2-(2-chloro-4-iodo-benzoyl)-malonate

Product 1

HCID 19081721Ethyl 3-(2-chloro-4-iodo-phenyl)-3-oxo-propionateYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

mc) 70.3 g of diethyl 2-(2-chloro-4-iodo-benzoyl)-malonate are heated to boiling under reflux for 6 hrs. while stirring vigorously with 750 ml of water and 0.75 g of p-toluenesulphonic acid. The reaction mixture is cooled to room temperature and extracted three times with 200 ml of diethyl ether each time. The ether phases are washed twice with 200 ml of saturated, aqueous sodium chloride solution each time, dried over magnesium sulphate and concentrated. 53.7 g (92%) of ethyl 3-(2-chloro-4-iodo-phenyl)-3-oxo-propionate are obtained as a yellowish oil. Mass spectrum: peaks inter alia at 352 (M+, 3%), 317 (73%), 289 (19%), 265 (100%).

Workup

  1. temperatureunder reflux for 6 hrs
  2. extractionextracted three times with 200 ml of diethyl ether each time
  3. washThe ether phases are washed twice with 200 ml of saturated, aqueous sodium chloride solution each time
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e2b105f36ec84d3e85f0947026c56318
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

Loading…