Methyl iodide → Methyl 5-formyl-2-methoxybenzoate

HRID 1583028Notes

Reaction equation

HRID 1583028 reaction equation
CI.[CH:3]([C:5]1[CH:13]=C(C(O)=O)[C:8]([OH:14])=[CH:7][CH:6]=1)=[O:4].[C:15](=O)([O-])[O-].[Cs+].[Cs+].[C:21]([O:24][CH2:25]C)(=[O:23])[CH3:22]>CN(C)C=O>[CH3:15][O:14][C:8]1[CH:7]=[CH:6][C:5]([CH:3]=[O:4])=[CH:13][C:22]=1[C:21]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 692265-Formylsalicylic acid

Product 1

HCID 10856352Methyl 5-formyl-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (3.6 mL, 0.042 mol, 3.5 eq) was added dropwise to a stirred solution of 5-formylsalicylic acid (2.78 g, 0.017 mol, 1 eq) and cesium carbonate (16.36 g, 0.050 mol, 3 eq) in N,N-dimethylformamide (50 mL). The reaction mixture was stirred overnight, then diluted with ethyl acetate (100 mL) and the organic solution washed with water (100 mL), and brine (4×100 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to a cream coloured powder (2.8 g, 86%). 1H NMR (CDCl3) δ9.92 (s, 1H, O═C—H), 4.01 (s, 3H, CH3), 3.93 (s, 3H, CH3).

Workup

  1. washthe organic solution washed with water (100 mL), and brine (4×100 mL)
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. customevaporated in vacuo to a cream

Sources & evidence

ORD record
ord-ea816792f93d4e48b6ba5dff65177568
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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