Sodium Iodide → HCID 131725720, compound

HRID 1797338Notes

Reaction equation

HRID 1797338 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:12]=1[O:23][CH3:24].[I-:25].[Na+]>CC(C)=O>[I:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:12]=1[O:23][CH3:24]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 69037208HCID 69037208, compound

Product 1

HCID 131725720HCID 131725720, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

26.8 g (75.52 mmol) methyl (2E)-3-{4-[(8-chloroctyl)oxy]-3-methoxyphenyl}-2-propenoate was dissolved in 1000 ml acetone. 65.16 g (435.15 mmol) sodium iodide were added. The reaction suspension was heated at reflux temperature for 24 hours. The reaction mixture was partitioned between diethylether and water. The organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The crude product was recrystallised from 2-propanol yielded 30.1 g (90%) methyl (2E)-3-{4-[(8-iodoctyl)oxy]-3-methoxyphenyl}-2-propenoate as white crystals.

Workup

  1. temperatureThe reaction suspension was heated
  2. temperatureat reflux temperature for 24 hours
  3. customThe reaction mixture was partitioned between diethylether and water
  4. washThe organic phase was washed repeatedly with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe crude product was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-922c70e8e35d4ae0b5f5ee5f757f9b2c
Source dataset
uspto-grants-2006_04
Patent number
US07034098B2

Reaction notes

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