Hexane → Methyl 4-acetyl-2,6-dichlorophenoxyacetate

HRID 743815

Reaktionsgleichung

Reaktionsgleichung von HRID 743815
[H-].[Na+].CCCCCC.[CH3:9][C:10]([C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([OH:19])=[C:14]([Cl:20])[CH:13]=1)=[O:11].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C.O>[C:10]([C:12]1[CH:13]=[C:14]([Cl:20])[C:15]([O:19][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[C:16]([Cl:18])[CH:17]=1)(=[O:11])[CH3:9]

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 869201-(3,5-Dichloro-4-hydroxyphenyl)ethanone

Produkt 1

HCID 18918381Methyl 4-acetyl-2,6-dichlorophenoxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (50% w/w dispersion in mineral oil, 1.32 g) was treated under argon with repeated washes of hexane. The oil-free residue was suspended in dry DMF (10 ml) and, with stirring and cooling (ice-bath), a solution of 3,5-dichloro-4-hydroxyacetophenone (5.13 g) in dry DMF (15 ml) was added dropwise. Stirring was continued for 30 minutes when methyl bromoacetate (3.06 ml) was added dropwise and stirring was continued for a further 18 hours at ambient temperature. The reaction mixture was added to water, the mixture was extracted twice with ethyl acetate, the organic phases dried (MgSO4), filtered and then evaporated. The residue, after recrystallisation from hexane (250 ml), gave methyl 4-acetyl-2,6-dichlorophenoxyacetate, 4.25 g, as white crystals: NMR (d6DMSO) δ8.00 (2H, s), 4.80 (2H, s), 3.73 (3H, s), 2.59 (3H, s).

Aufarbeitung

  1. temperaturecooling (ice-bath)
  2. stirringStirring
  3. stirringstirring
  4. waitwas continued for a further 18 hours at ambient temperature
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. dry with materialthe organic phases dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue, after recrystallisation from hexane (250 ml)

Quellen und Nachweise

ORD-Eintrag
ord-b0149f6c7e52413f875b3b3e8c45e703
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556977

Verknüpfte Notizen

Wird geladen…