Sodium Iodide → (5-Iodo-pentyl)-cyclohexane

HRID 2063935Notes

Reaction equation

HRID 2063935 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[I-:13].[Na+]>CC(C)=O>[I:13][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Conditions

Temperature
60 °C

Procedure

A mixture of (5-bromopentyl)cyclohexane (2 gm, 8.6 mmol) in acetone (20 ml), and sodium iodide (2.57 g, 17.1533 mmol) was heated for 60° C. for 12 hrs. The mixture was allowed to cool to room temperature and the solvent was evaporated. The residue was diluted with EtOAc (30 ml), H2O (20 ml) was added, separated and the organic phase was washed with brine (30 ml). The organic layer was dried over anhydrous Na2SO4; solvent was evaporated under reduced pressure and the crude product was purified by column chromatography using hexane as eluent. The pure product was an oily liquid (1.36 gm).

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was evaporated
  3. additionThe residue was diluted with EtOAc (30 ml), H2O (20 ml)
  4. additionwas added
  5. customseparated
  6. washthe organic phase was washed with brine (30 ml)
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. customsolvent was evaporated under reduced pressure
  9. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-51578071c53d4fd1bc0939868f486bb0
Source dataset
uspto-grants-2012_10
Patent number
US08288410B2

Reaction notes

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