Methyl iodide → 2-Methoxypropiophenone

HRID 916226Notes

Reaction equation

HRID 916226 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. customTLC, Rf 0.55 (1% MeOH:1% IPA:CHCl3) GC, tr 4.58 min

Sources & evidence

ORD record
ord-12178347044140d0a94eeb3ca9a0b7db
Source dataset
uspto-grants-2007_09
Patent number
US07268166B2

Reaction notes

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