Sodium Iodide → (R)-3-iodo-1-phenyl-1-propanol

HRID 2218077Notes

Reaction equation

HRID 2218077 reaction equation
Cl[CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[I-:12].[Na+]>CC(C)=O>[I:12][CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 642409(1R)-3-chloro-1-phenylpropan-1-ol

Product 1

HCID 14476875(R)-3-iodo-1-phenyl-1-propanolYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (R)-(+)-3-chloro-1-phenyl-1-propanol (5 g, 29.3 mmol) in acetone (50 mL) was added sodium iodide (4.83 g, 32.2 mmol). The resulting solution was heated at reflux for 16 h. The solution was cooled, filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting silica gel with hexane: ethyl acetate [100:0 to 3:1] to yield the title compound as a white solid (7.51 g, 98%); δH (300 MHz, CDCl3) 7.36 (5H, m, Ar), 4.83 (1H, m, O—CH), 3.34-3.15 (2H, m, CH2), 2.28-2.15 (2H, m, CH2).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 16 h
  3. temperatureThe solution was cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting silica gel with hexane

Sources & evidence

ORD record
ord-35d99c2432b14763876412b606f19608
Source dataset
uspto-grants-2008_08
Patent number
US07410982B2

Reaction notes

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