Chloromethyl Methyl Ether → 1-Iodo-4-(methoxymethoxy)benzene

HRID 2415235Notes

Reaction equation

HRID 2415235 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][O:12][CH2:13]Cl.C(OC(=O)C)C.O>CN(C)C=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 108944-IodophenolHCID 24758Sodium hydrideHCID 22728543Water ethylacetate

Product 1

HCID 110327301-Iodo-4-(methoxymethoxy)benzeneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g (22.7 mmol) of 4-iodophenol are added to a suspension or 75% sodium hydride (872 mg; 27.25 mmol) in 20 ml of dimethylformamide. The mixture is stirred for 30 minutes at room temperature and 2.59 ml (34.1 mmol) of methoxymethyl chloride are then added. The solution is stirred for 2 h and the medium is then poured into an ethylacetate/water mixture. After separation of the phases by settling, the organic phase is washed twice with water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. 5.74 g (96%) of a colourless oil are obtained.

Workup

  1. stirringThe solution is stirred for 2 h
  2. customAfter separation of the phases
  3. washthe organic phase is washed twice with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator under vacuum at 40° C

Sources & evidence

ORD record
ord-210b1ef63c49433cbda7bbc21a3d18f7
Source dataset
uspto-grants-2004_11
Patent number
US06818666B2

Reaction notes

Loading…