Sodium Iodide → Ethyl [3-(3-iodopropyl)phenoxy]acetate

HRID 2389354Notes

Reaction equation

HRID 2389354 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)[O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=O)=O.[I-:22].[Na+].CCOC(C)=O>CC(C)=O>[I:22][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)[O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 86637907Ethyl (3-{3-[(methylsulfonyl)oxy]propyl}phenoxy)acetate

Product 1

HCID 86637892Ethyl [3-(3-iodopropyl)phenoxy]acetateYield 83.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl (3-{3-[(methylsulfonyl)oxy]propyl}phenoxy)acetate (155 g) in acetone (1.55 L) was added sodium iodide (293.7 g) at ambient temperature and the mixture was stirred at the same temperature for 18 hours. EtOAc (1 L) was added to the mixture at ambient temperature and the resulting mixture was washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford ethyl [3-(3-iodopropyl)phenoxy]acetate (142 g) as a red oil.

Workup

  1. washthe resulting mixture was washed successively with water and brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b3e8e004cf4e4ddf9e6d9b2e2cf54fda
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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