Dimethylformamide → Methyl 5-formyl-2-methoxybenzoate

HRID 391399

Reaktionsgleichung

Reaktionsgleichung von HRID 391399
[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]

Komponenten

5

Edukt 4

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

Produkt 1

HCID 10856352Methyl 5-formyl-2-methoxybenzoate

Versuchsvorschrift

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)+.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-3b106c7bd96341599a201faee0911a6c
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

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