2',4'-Dihydroxyacetophenone → 4'-Benzyloxy-2'-hydroxyacetophenone

HRID 858662

Reaktionsgleichung

Reaktionsgleichung von HRID 858662
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=1[C:23](=[O:25])[CH3:24]>CN(C=O)C>[CH2:7]([O:22][C:20]1[CH:19]=[CH:18][C:17]([C:23](=[O:25])[CH3:24])=[C:16]([OH:15])[CH:21]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 69902',4'-DihydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Produkt 1

HCID 3092574'-Benzyloxy-2'-hydroxyacetophenoneAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium carbonate (27.2 g, 0.2 mol) followed by benzyl bromide (7.04 mL, 59.2 mmol) were added to a solution of 1-(2,4-dihydroxy-phenyl)-ethanone (10 g, 66 mmol) in DMF (90 mL): The mixture was stirred for 2 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) followed by recrystallization gave the title compound as a white solid (8.7 g, 55%). 1H NMR (400 MHz, CDCl3): δ 2.55 (s, 3 H), 5.09 (s, 2 H), 6.50 (s, 1 H), 6.51 (dd, J=9.1, 3.9 Hz, 1 H), 7.34–7.43 (m, 5 H), 7.64 (d, J=9.1 Hz, 1 H), 12.73 (s, 1 H).

Aufarbeitung

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)
  6. customfollowed by recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-fe87ee52d494475cb97c0477906d1d46
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148226B2

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