Methyl iodide → 1-(3-Hydroxy-5-methoxyphenyl)ethanone

HRID 217740

Reaction equation

HRID 217740 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([OH:8])[CH:7]=1.[CH3:12]I.[H-].[Na+]>CN(C=O)C.CC(=O)OCC>[OH:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([O:8][CH3:12])[CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1039933',5'-Dihydroxyacetophenone

Product 1

HCID 193506661-(3-Hydroxy-5-methoxyphenyl)ethanoneYield 34.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-(3,5-Dihydroxyphenyl)ethanone (3 g) and methyl iodide (2.80 g) were dissolved in DMF (40 ml), and sodium hydride (568 mg) was added. After stirring at RT for 2 h, the DMF was drawn off. The residue was taken up in EA and washed with water, dried, filtered and concentrated. The residue was purified using silica gel (89 g cartridge, n-heptane/EA 0-50% within 30 min). 1.12 g of the title compound were obtained.

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customsilica gel (89 g cartridge, n-heptane/EA 0-50% within 30 min)

Sources & evidence

ORD record
ord-f95df772e1fa45d7b30c9cdf1ff92fb1
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Linked notes

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