Sodium Iodide → 1-(3-Iodopropyl)-4-methoxybenzene

HRID 704402

Reaction equation

HRID 704402 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=O)=O.[I-:17].[Na+]>CC(C)=O>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][I:17])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 116659383-(4-Methoxyphenyl)propyl methanesulfonate

Product 1

HCID 140406651-(3-Iodopropyl)-4-methoxybenzeneYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 6.30 g of 3-(4-methoxyphenyl)propyl methanesulfonate and 11.1 g of sodium iodide in 100 ml of acetone was refluxed for 15 hours. The reaction mixture was concentrated under reduced pressure and, after addition of water, the residue was extracted with ether. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 6.62 g of 3-(4-methoxyphenyl)propyl iodide.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionafter addition of water
  3. extractionthe residue was extracted with ether
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-169f61b8947e4eea92bcc75a0d45316c
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Linked notes

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