Acetonitrile → Ethyl (4-formyl-2-methylphenoxy)acetate

HRID 1269589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269589
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C(#N)C.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:3]([CH3:10])[CH:4]=1)=[O:7]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 1399014-Hydroxy-3-methylbenzaldehyde

Produkt 1

HCID 58622891Ethyl (4-formyl-2-methylphenoxy)acetateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-3-methylbenzaldehyde (8 g, 58.8 mmol) in an hydrous acetonitrile (300 mL), under nitrogen at 0° C., was added caesium carbonate (21 g, 64.6 mmol) and ethyl bromoacetate (6.52 mL, 58.8 mmol). The resulting mixture was allowed to come to room temperature and stirred for 16 h. The reaction mixture was diluted with water (400 mL) and extracted with EtOAc (2×500 mL). The combined organic extracts were dried (MgSO4) and the solvents removed in vacuo, to afford the title compound as brown solid (11.5 g).

Aufarbeitung

  1. customto come to room temperature
  2. extractionextracted with EtOAc (2×500 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customthe solvents removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-473f17f55b5d4d3d9b9c45fd62fa22b3
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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