Dimethylformamide → Methyl 5-formyl-2-methoxybenzoate

HRID 391391

Reaction equation

HRID 391391 reaction equation
[CH:1]([C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6](O)=[CH:5][CH:4]=1)=[O:2].CI.[C:15](=O)([O-])[O-].[K+].[K+].CN(C)[CH:23]=[O:24]>>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:24][CH3:23])=[C:7]([CH:11]=1)[C:8]([O:10][CH3:15])=[O:9])=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 692265-Formylsalicylic acid

Product 1

HCID 10856352Methyl 5-formyl-2-methoxybenzoate

Procedure

5-Formyl salicylic acid (2.0 g, 12.0 mmol), methyl iodide (1.5 mL, 25 mmol) and potassium carbonate (3.06 g, 22.2 mmol) were combined in dimethylformamide (15 mL). After stirring at room temperature for 16 h, the solvent was removed in vacuo and the crude product dissolved in ethyl acetate, washed with water (2×), brine (2×), dried over sodium sulfate, concentrated, and purified by column chromatography to afford 1.85 g (79%). 1H-NMR (CDCl3, 500 MHz) δ 9.91 (s, 1H), 8.31 (d, J=2.1 Hz, 1H), 8.02 (dd, J=8.5, 2.5 Hz, 1H), 7.11 (d, J=8.6 Hz, 1H), 3.99 (s, 3H), 3.91 (s, 3H). Mass spec.: 195.05 (MH)+.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe crude product dissolved in ethyl acetate
  3. washwashed with water (2×), brine (2×)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography
  7. customto afford 1.85 g (79%)

Sources & evidence

ORD record
ord-58de6570e4f94d8e9e81d3b1ab9559d4
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Linked notes

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