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

HRID 1822947Notes

Reaction equation

HRID 1822947 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-6f4743f794d84e83935a1ab25a2e56f0
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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