Sodium Hydroxide → 3,3-Diphenylpropanal

HRID 254257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254257
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH:9]=[O:10])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 299083,3-DiphenylpropanolHCID 159087Triacetoxyperiodinane

Produkt 1

HCID 110746643,3-DiphenylpropanalAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4.69 mL (23.55 mmol, 1 eq.) of 3,3-diphenylpropanol are dissolved in 100 mL of CH2Cl2 under argon. 10.5 g (24.73 mmol, 1.05 eq.) of Dess Martin Periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) are added to the mixture and the solution is stirred for 1 hour 30 min at 0° C. 100 mL of 2 M sodium hydroxide and 100 mL of CH2Cl2 are then added. The organic phase is washed with 2 M sodium hydroxide (twice), with water (twice), dried over MgSO4, filtered and concentrated. The crude reaction product is subjected to chromatography over silica gel (eluent: 5/1 heptane/AcOEt). An oil which crystallises in the form of a white product is recovered (4.76 g, yield=96%).

Aufarbeitung

  1. washThe organic phase is washed with 2 M sodium hydroxide (twice), with water (twice),
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude reaction product
  6. customAn oil which crystallises in the form of a white product
  7. customis recovered (4.76 g, yield=96%)

Quellen und Nachweise

ORD-Eintrag
ord-eb2643c61e08458ba21d3a1f38de6564
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875609B2

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