Ethylene carbonate → 3-(2-Hydroxy-ethoxy)-5-methoxy-benzaldehyde

HRID 591853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591853
OC1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].[O:12]1[CH2:16][CH2:15][O:14][C:13]1=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:12][CH2:16][CH2:15][O:14][C:13]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6]

Komponenten

5

Edukt 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 53145613-Hydroxy-5-methoxybenzaldehyde

Produkt 1

HCID 866620393-(2-Hydroxy-ethoxy)-5-methoxy-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

3-Hydroxy-5-methoxy-benzaldehyde (12.0 g, 78.9 mmol) and [1,3]dioxolan-2-one (13.9 g, 157.0 mmol) in anhydrous DMF (50 mL) was added potassium carbonate (21.6 g, 157.0 mmol). The mixture was then heated to 110° C. for 16 hours. The reaction mixture was cooled to room temperature. Solid potassium carbonate was filtered and washed with ethyl acetate. The organic phase was collected and solvent was removed. The residue was purified by column chromatography (silica gel 230-400 mesh; eluting with dichloromethane and ethyl acetate 7:1), to give 3-(2-hydroxy-ethoxy)-5-methoxy-benzaldehyde as a brown liquid. Yield: 10.0 g (65%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationSolid potassium carbonate was filtered
  3. washwashed with ethyl acetate
  4. customThe organic phase was collected
  5. customsolvent was removed
  6. customThe residue was purified by column chromatography (silica gel 230-400 mesh; eluting with dichloromethane and ethyl acetate 7:1)

Quellen und Nachweise

ORD-Eintrag
ord-ed59e5e67b55441798b1201219e2ea37
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238640B2

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