Butyl iodide → n-Butyl 5-formyl-2-hydroxybenzoate

HRID 259778

Reaktionsgleichung

Reaktionsgleichung von HRID 259778
[CH:1]([C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1)=[O:2].[CH2:13](I)[CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([CH:11]=1)[C:8]([O:10][CH2:13][CH2:14][CH2:15][CH3:16])=[O:9])=[O:2]

Komponenten

5

Edukt 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 692265-Formylsalicylic acid

Produkt 1

HCID 18930712n-Butyl 5-formyl-2-hydroxybenzoateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Formylsalicylic acid (5.0 g, 30 mmol), n-butyl iodide (3.4 mL, 30 mmol), and potassium carbonate (4.2 g, 30 mmol) were stirred in DMF (40 mL) for 27 h at room temperature. After several EtOAc/H2O extractions, the mixture was dried (MgSO4), and concentrated. Chromatography on silica gel, eluting with 5% to 30% EtOAc in hexanes, followed by solvent removal gave a white solid (2.0 g). HR-MS: Calc'd 223.0970, Found 223.0968. Anal. Calc'd for C12H14O4 : C, 64.84; H, 6.36; Found: C, 64.82; H, 6.30.

Aufarbeitung

  1. extractionAfter several EtOAc/H2O extractions
  2. dry with materialthe mixture was dried (MgSO4)
  3. concentrationconcentrated
  4. washChromatography on silica gel, eluting with 5% to 30% EtOAc in hexanes
  5. customfollowed by solvent removal

Quellen und Nachweise

ORD-Eintrag
ord-ace64d6fc71645eea4ffe28f4bb8114c
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05523302

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