1-(Benzyloxy)propan-2-ol → 1-(Benzyloxy)propan-2-one

HRID 399104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399104
[CH2:1]([O:8][CH2:9][CH:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>CN(C=O)C.O>[CH2:1]([O:8][CH2:9][C:10](=[O:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 2959551-(Benzyloxy)propan-2-olHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 36912841-(Benzyloxy)propan-2-oneAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

3-Benzyoxypropan-2-ol 16 (40 g, 0.24 mol) was added to a suspension of pyridinium chlorochromate (155.2 g, 0.72 mol) in DMF (150 ml) at 25° C., stirred at 65° C. for 3 h, and then diluted with water (75 mL) (Step 14). The mixture was extracted with ether (2×50 mL) and the combined ether layers were washed with water (3×50 mL) dried (MgSO4) and the solvent removed by roto-evaporation. Distillation gave 31 g (77%) of 3-benzyloxypropan-2-one; 17 bp 104-106 (10 mm). 1H NMR (CDCl3) δ2.16 (s, 3H, CH3), 4.05 (s, 1H, OH), 4.59 (s, 2H, OCH2), 7.5 (s, 5H, phenyl).

Aufarbeitung

  1. extractionThe mixture was extracted with ether (2×50 mL)
  2. washthe combined ether layers were washed with water (3×50 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed by roto-evaporation
  5. distillationDistillation

Quellen und Nachweise

ORD-Eintrag
ord-071ec0f206a04182956109c495402c56
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817776

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