Methyl iodide → Methyl 5-acetyl-2-methoxybenzoate

HRID 450885Notes

Reaction equation

HRID 450885 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:15](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C.C(OCC)(=O)C>[CH3:15][O:1][C:2]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 606426Methyl 5-acetyl-2-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Methyl 2-hydroxy-5-acetylbenzoate (12 g, 61.7 mmol) in DMF (200 ml) was added cesium carbonate (24.15 g, 74.1 mmol) and MeI (9.64 g, 68 mmol). The reaction mixture was stirred for 16 hours at 0° C. and then diluted with ethyl acetate, washed with aq Na2S2O5, brine, dried over Na2SO4, filtered and concentrated. The purification was done by flash chromatography on silica gel column (ethyl acetate:hexane 1:2) to provide the title compound as an off white solid.

Workup

  1. washwashed with aq Na2S2O5, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe purification

Sources & evidence

ORD record
ord-2e57aab471d944faaa1792da25d0ac80
Source dataset
uspto-grants-2013_07
Patent number
US08487000B2

Reaction notes

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