Methyl iodide → 1-(5-Chloro-2-methoxyphenyl)ethanone

HRID 1616582Notes

Reaction equation

HRID 1616582 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[C:12]([O-])([O-])=O.[K+].[K+].CI>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 740613-Chloro-6-hydroxyacetophenone

Product 1

HCID 2404341-(5-Chloro-2-methoxyphenyl)ethanoneYield 79.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

Dissolve 5′-chloro-2′-hydroxyacetophenone (15.3594 g, 90.03 mmol) in 100 mL of anhydrous acetonitrile in a pressure vessel. Add K2CO3 (13.7541 g, 99.52 mmol) and MeI (25.56 mL, 180.06 mmol) to the vessel. Seal the vessel and heat the reaction mixture to 85° C. for 18 hours. Cool the reaction and concentrate it in vacuo. Partition the residue between Et2O and H2O. Wash the organic layers with 2N NaOH (2×). Dry the combined organic layers with MgSO4. Filter off the drying agent and concentrate in vacuo to afford 13.15 g of 1-(5-chloro-2-methoxy-phenyl)-ethanone (79%).

Workup

  1. customSeal the vessel
  2. temperatureCool
  3. customthe reaction
  4. concentrationconcentrate it in vacuo
  5. customPartition the residue between Et2O and H2O
  6. washWash the organic layers with 2N NaOH (2×)
  7. dry with materialDry the combined organic layers with MgSO4
  8. filtrationFilter off the drying agent
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9c106dbcefec40f1a687b2472ddcc47b
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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