Butyl iodide → 6-Butoxy-2,2-dimethylchroman-4-one

HRID 613442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 613442
[CH3:1][C:2]1([CH3:14])[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:13])[CH:8]=2)[O:3]1.[H-].[Na+].I[CH2:18][CH2:19][CH2:20][CH3:21]>CN(C=O)C>[CH2:18]([O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:14])([CH3:1])[CH2:11][C:10]2=[O:12])[CH2:19][CH2:20][CH3:21]

Komponenten

5

Edukt 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 35198596-Hydroxy-2,2-dimethylchroman-4-one

Produkt 1

HCID 110540056-Butoxy-2,2-dimethylchroman-4-oneAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 50 g (0.26 mol) of 2,2-dimethyl-6-hydroxychroman-4-one (Example 1a) in 500 ml of DMF was added dropwise to a suspension of 9.0 g (0.3 mol) of 80 percent sodium hydride in 500 ml of DMF. The mixture was stirred at RT for 90 min, 49 g (0.265 mol) of iodobutane were added and the mixture was stirred at RT for a further 90 min. The reaction mixture was then concentrated under reduced pressure and the residue was admixed with water and extracted repeatedly with EA. The organic phases were washed with 5 M aqueous sodium hydroxide solution, stirred with activated carbon and magnesium sulfate, filtered and concentrated. This procedure gave 57.6 g of 6-butoxy-2,2-dimethylchroman-4-one.

Aufarbeitung

  1. stirringthe mixture was stirred at RT for a further 90 min
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. extractionextracted repeatedly with EA
  4. washThe organic phases were washed with 5 M aqueous sodium hydroxide solution
  5. stirringstirred with activated carbon and magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a770b73c42424de495e2daaa0324c2b4
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008245

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