Dimethylformamide → Methyl 5-formyl-2-methoxybenzoate

HRID 391383

Reaction equation

HRID 391383 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-f270e27761094ef88c0a415206d73b14
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Linked notes

Loading…