Isopropyl iodide → 2-Isopropoxy-4-methoxybenzonitrile

HRID 1167303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167303
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].I[CH:19]([CH3:21])[CH3:20]>C(O)C.C(OCC)C.O>[CH:19]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])([CH3:21])[CH3:20]

Komponenten

7

Edukt 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 114236802-Hydroxy-4-methoxybenzonitrile

Produkt 1

HCID 227210812-Isopropoxy-4-methoxybenzonitrileAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 2-hydroxy-4-methoxy-benzonitrile (16.4 g, 134.1 mmol) in ethanol were added potassium carbonate (37.07 g, 268.2 mmol) and 2-iodopropane (40.16 mL, 402.3 mmol). The reaction mixture was heated at gentle reflux for 3.5 h. The solvent was removed to afford a brown paste. It was then taken in diethyl ether (300 mL) and water (200 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (3×100 mL). The combined organic extracts were washed with brine and dried over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 12% ethyl acetate in hexanes yielded 2-isopropoxy-4-methoxy-benzonitrile as a pale-yellow oil (11.8 g, 56%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat gentle reflux for 3.5 h
  3. customThe solvent was removed
  4. customto afford a brown paste
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with diethyl ether (3×100 mL)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe solid was then filtered off
  10. concentrationthe filtrate was concentrated in vacuo
  11. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  12. washeluting with 12% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3d12bfd886f549729fb2df667d01fa0d
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617346B1

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