Methyl iodide → 2-Methoxypropiophenone

HRID 322558Notes

Reaction equation

HRID 322558 reaction equation
[OH:1][CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].IC.[C:14]([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(OCC)C>[CH3:14][O:1][CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1011212-Hydroxy-1-phenyl-1-propanone

Product 1

HCID 113097012-Methoxypropiophenone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-hydroxypropiophenone (3.00 g, 20.0 mmol), iodomethane (3.40 g, 24.0 mmol), and K2CO3 (granular, anh.; 13.8 g, 99.9 mmol) was refluxed in acetone (75 mL) for 18 h. The reaction mixture was cooled to room temperature and the inorganic salts were removed by filtration. The filtrate was evaporated under vacuum to give an oil which was subsequently dissolved in diethyl ether (200 mL) and then washed with 0.1N NaOH (3×50 mL) followed by H2O (50 mL). The organic layer was dried (anh. Na2SO4), filtered, and evaporated to an orange oil (3.17 g, 96.9%). This material was used in the following step without further purification. TLC, Rf 0.55 (1% MeOH:1% IPA:CHCl3); GC, tr 4.58 min; MS, m/z 164 (M+1).

Workup

  1. customthe inorganic salts were removed by filtration
  2. customThe filtrate was evaporated under vacuum
  3. customto give an oil which
  4. washwashed with 0.1N NaOH (3×50 mL)
  5. dry with materialThe organic layer was dried (anh. Na2SO4)
  6. filtrationfiltered
  7. customevaporated to an orange oil (3.17 g, 96.9%)
  8. customThis material was used in the following step without further purification
  9. customtr 4.58 min

Sources & evidence

ORD record
ord-e15b3a7003e045edadd4160fbd2aa37f
Source dataset
uspto-grants-2001_04
Patent number
US06211245B1

Reaction notes

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