Ethyl Acetate → Methyl 2-(2-chloro-4-methylphenoxy)-2-phenylacetate

HRID 1609527

Reaktionsgleichung

Reaktionsgleichung von HRID 1609527
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[OH:11].Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(OCC)(=O)C>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[O:11][CH:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:13]=1)[C:20]([O:22][CH3:23])=[O:21]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 148512-Chloro-4-methylphenolHCID 24758Sodium hydrideHCID 8063364Methyl 2-(2-bromophenyl)acetate

Produkt 1

HCID 19385673Methyl 2-(2-chloro-4-methylphenoxy)-2-phenylacetateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of 0.282 g (7.04 mmol) of a 60% oil dispersion of sodium hydride in DMF was added 1.00 g (7.04 mmol) of 2-chloro-4-methylphenol and the mixture was stirred under an N2 atmosphere at room temperature. After 10 minutes, a solution of 1.94 g (8.45 mmol) of methyl 2-bromophenylacetate dissolved in 10 mL of DMF was added and the reaction was stirred an additional 1.5 hours. The reaction was then diluted into ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 4% ethyl acetate/hexane to afford 1.70 g (83%) of the title compound.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction was stirred an additional 1.5 hours
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 4% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-cd49721ed4c64165be330ebe474c3f22
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05401745

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