Sodium Iodide → 1-(2-Iodoethyl)-4-octylbenzene

HRID 1505021Notes

Reaction equation

HRID 1505021 reaction equation
[CH2:1]([C:9]1[CH:21]=[CH:20][C:12]([CH2:13][CH2:14]CS([O-])(=O)=O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[I-:22].[Na+]>O1CCCC1>[I:22][CH2:14][CH2:13][C:12]1[CH:20]=[CH:21][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86730728HCID 86730728, compound

Product 1

HCID 105453621-(2-Iodoethyl)-4-octylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Octylphenethylmethane sulfonate (70 g) and dry tetrahydrofuran (500 mL) are charged into a 1 liter single-neck round bottom flask, equipped with a calcium chloride guard tube and shielded with light protecting black cover. The mixture is stirred for 10 minutes, then sodium iodide (133 g) is added and the mixture is stirred overnight at room temperature. The solvent is evaporated under vacuum and the residue is dissolved in water (300 mL) and extracted with ethyl acetate (2×250 mL). Ethyl acetate extracts are combined, washed with aqueous sodium thiosulphate, dried with sodium sulphate, and concentrated under vacuum to give the title compound. Yield: 70 g.

Workup

  1. customequipped with a calcium chloride guard tube
  2. stirringthe mixture is stirred overnight at room temperature
  3. customThe solvent is evaporated under vacuum
  4. dissolutionthe residue is dissolved in water (300 mL)
  5. extractionextracted with ethyl acetate (2×250 mL)
  6. washwashed with aqueous sodium thiosulphate
  7. dry with materialdried with sodium sulphate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e3d1d0704e15403fbf59da90094d2b03
Source dataset
uspto-grants-2015_12
Patent number
US09216943B2

Reaction notes

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