Water → 1-Iodo-4-(methoxymethoxy)benzene

HRID 1006935Notes

Reaction equation

HRID 1006935 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH3:15][O:16][CH2:17]Cl.O>CN(C=O)C>[CH3:15][O:16][CH2:17][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 108944-IodophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 110327301-Iodo-4-(methoxymethoxy)benzeneYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Paraiodophenol (25 g) was dissolved in DMF (100 ml), followed by the addition of potassium t-butoxide (25 g) and methoxymethyl chloride (13 ml), and the mixture was reacted at 60° C. overnight. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried and evaporated. The resulting residue was subjected to a silica gel short column, to give 4-methoxymethoxy-1-iodobenzene as an oil (26.5 g, yield; 88%).

Workup

  1. customthe mixture was reacted at 60° C. overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-4e438ca9e2814da780f5c062773f8a4a
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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