Chloromethyl Methyl Ether → 2-Benzyl-1-methoxymethyloxy-4-iodobenzene

HRID 2216349

Reaction equation

HRID 2216349 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12]([I:14])[CH:11]=[CH:10][C:9]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][CH2:18]Cl.O1CCCC1.[H-].[Na+]>O>[CH2:1]([C:8]1[CH:13]=[C:12]([I:14])[CH:11]=[CH:10][C:9]=1[O:15][CH2:16][O:17][CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 219422992-Benzyl-4-iodophenol

Product 1

HCID 219423042-Benzyl-1-methoxymethyloxy-4-iodobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.1 g of 2-benzyl-1-hydroxy-4-iodobenzene and 3 ml of chloromethyl methyl ether were added to 100 ml of tetrahydrofuran and while stirring on an ice bath, 1.45 g of 60% (oily) sodium hydride was added dropwise to the mixture. After stirring for 2 hours, water was added to the reaction mixture, which then was extracted with ethyl acetate, washed with saturated brine and thereafter dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography with 10% ethyl acetate/hexane, to give 8.7 g of the title compound.

Workup

  1. stirringAfter stirring for 2 hours
  2. extractionthen was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified by silica gel column chromatography with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d1ca98b4f2744c7490f5e8fb06c967dd
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Linked notes

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