Thionyl Chloride → Methyl 3-(3-iodophenyl)propionate

HRID 1352879Notes

Reaction equation

HRID 1352879 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[C:17](=O)([O-])O.[Na+]>CO>[I:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:17])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 38702213-(3-Iodophenyl)propionic acid

Product 1

HCID 22928694Methyl 3-(3-iodophenyl)propionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of the mixture of 3-(3-iodophenyl)propionic acid (12.0 g) in methanol (200 ml) was added thionyl chloride (11.0 g, 92.5 mmol), and the mixture was stirred for 30 minutes at 40° C. To the mixture was added an aqueous saturated sodium hydrogencarbonate solution and the mixture was extracted with toluene:ethyl acetate (1:1). The organic layer was washed with water and an aqueous saturated sodium chloride solution, and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was separated and purified with silica gel chromatography (hexane:ethyl acetate=5:1→4:1) to give the subject compound (9.66 g, 61%:total of 3 steps).

Workup

  1. extractionthe mixture was extracted with toluene:ethyl acetate (1:1)
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated sodium chloride solution, and dried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was separated
  6. custompurified with silica gel chromatography (hexane:ethyl acetate=5:1→4:1)
  7. customto give the subject compound (9.66 g, 61%:total of 3 steps)

Sources & evidence

ORD record
ord-d164afe14fa04cc7ab7a21ca39a4a574
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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