Dimethylformamide → Methyl 5-formyl-2-methoxybenzoate

HRID 391383

반응식

HRID 391383 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

HCID 10856352Methyl 5-formyl-2-methoxybenzoate

실험 절차

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)+.

후처리

  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%)

출처 및 근거

ORD 기록
ord-f270e27761094ef88c0a415206d73b14
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383821B2

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