Sodium Iodide → 1-[4-(Methoxymethyl)phenyl]propan-2-one

HRID 434367Notes

Reaction equation

HRID 434367 reaction equation
C1[O:15][C:4]([CH3:14])([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12]Br)=[CH:8][CH:7]=2)OC1.[CH3:16][O-:17].[Na+].[I-].[Na+]>CO>[CH3:16][O:17][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4](=[O:15])[CH3:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 10942334Sodium MethoxideHCID 566280772-{[4-(Bromomethyl)phenyl]methyl}-2-methyl-1,3-dioxolane

Product 1

HCID 204938201-[4-(Methoxymethyl)phenyl]propan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

1-(4-Bromomethylphenyl)propan-2-one ethylene ketal (1.35 g) in methanol was added to sodium methoxide (from sodium (0.11 g)) in methanol containing a trace of sodium iodide. The mixture was refluxed for 1 hour. Methanol was removed, the residue partitioned between water and ether and the combined organic extracts dried. Removal of the solvent gave an oil which was dissolved in methanol-2 N hydrochloric acid and left for 1 hour at room temperature. Extraction with ether gave the title compound, bp 106°/0.7 mm. τ(CDCl3) 7.9 (3H, s), 7.63 (3H, s), 6.33 (2H, s), 5.54 (2H, s), 2.8 (2H, d, J=8 Hz), 2.6 (2H, d, J=8 Hz).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customMethanol was removed
  3. customthe residue partitioned between water and ether
  4. customthe combined organic extracts dried
  5. customRemoval of the solvent
  6. customgave an oil which
  7. extractionExtraction with ether

Sources & evidence

ORD record
ord-0ef15178418849c9ae0a69c2616abdf3
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

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