Sodium Iodide → HCID 19757191, compound

HRID 1588129Notes

Reaction equation

HRID 1588129 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:15]([O:16][CH2:17][O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=[C:12]([O:22][CH2:23][O:24][CH3:25])[C:11]=1[O:26][CH3:27])(=O)=O.[I-:28].[Na+]>CC(C)=O.CN(C)P(=O)(N(C)C)N(C)C>[I:28][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:15]([O:16][CH2:17][O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=[C:12]([O:22][CH2:23][O:24][CH3:25])[C:11]=1[O:26][CH3:27]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 19757237HCID 19757237, compound

Product 1

HCID 19757191HCID 19757191, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
70 °C

Procedure

1.5 Grams of 4-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]butyl methanesulfonate was dissolved in a mixed solvent of 40 ml of acetone with 4 ml of hexamethylphosphoric triamide, then 2 g of sodium iodide was added to thereto and the whole mixture was heated at 70° C. in an oil bath and stirred for 1.5 hours. After the completion of the reaction, the reaction mixture was concentrated under a reduced pressure, then 200 ml of diethyl ether was added thereto, and washed twice with 100 ml of water, further washed twice with 100 ml of a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. Concentrated under reduced pressure to yield 1.3 g of 1-(4-iodobutyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene. Colorless oily substance.

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction mixture was concentrated under a reduced pressure
  3. addition200 ml of diethyl ether was added
  4. washwashed twice with 100 ml of water
  5. washfurther washed twice with 100 ml of a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentrated under reduced pressure

Sources & evidence

ORD record
ord-e214d1627bad40e69ccc801c960384b7
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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