Chloromethyl Methyl Ether → 1-(2-Hydroxy-4-iodo-5-methoxy-phenyl)-ethanone

HRID 38386Notes

Reaction equation

HRID 38386 reaction equation
[H-].[Na+].[I:3][C:4]1[C:5]([O:14][CH3:15])=[CH:6][C:7]([C:11](=[O:13])[CH3:12])=[C:8]([OH:10])[CH:9]=1.[Na].ClCOC>CN(C=O)C>[OH:10][C:8]1[CH:9]=[C:4]([I:3])[C:5]([O:14][CH3:15])=[CH:6][C:7]=1[C:11](=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 67296262Sodium 5-iodo-2-acetyl,4-methoxyphenol

Product 1

HCID 595986051-(2-Hydroxy-4-iodo-5-methoxy-phenyl)-ethanoneYield 107.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To suspension of sodium hydride (0.044 g, 1.1 mmol, 60% in mineral oil) in 0.5 ml DMF was added sodium 5-iodo-2-acetyl,4-methoxyphenol (0.292 g, 1 mmol, prepared as described in Example 35) as a solution in 1.5 ml DMF. After 10 minutes chloromethoxy methane (0.079 g, 1.0 mmol) was added. After 30 minutes the mixture was extracted with CH2Cl2. The The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (88:12=hexane/ethyl acetate) afforded 1-(2-hydroxy-4-iodo-5-methoxy-phenyl)-ethanone (0.314 g, 85%) as yellow solid; [MH]+=337.

Workup

  1. extractionAfter 30 minutes the mixture was extracted with CH2Cl2
  2. washThe The combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via flash chromatography (88:12=hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b0b0a0b52c714f3b88bca4e5272d575c
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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