Water → 4-(2-Phenylpropan-2-yl)benzaldehyde

HRID 1025537

Reaktionsgleichung

Reaktionsgleichung von HRID 1025537
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].N12CC3CC(CC(C3)C1)C2.O.[C:27]([O-])([O-])=[O:28].[K+].[K+]>C(O)(C(F)(F)F)=O>[C:10]1([C:2]([C:4]2[CH:9]=[CH:8][C:7]([CH:27]=[O:28])=[CH:6][CH:5]=2)([CH3:1])[CH3:3])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13065DimethyldiphenylmethaneHCID 1361061-Azatricyclo(3.3.1.13,7)decane

Produkt 1

HCID 185094134-(2-Phenylpropan-2-yl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of propane-2,2-diyldibenzene (3.93 g, 20 mmol) and 1-aza-tricyclo[3.3.1.1*3,7*]decane (2.80 g, 20 mmol) in TFA (35 mL) was heated at 100° C. for 16 h. The reaction mixture was allowed to cool to RT, poured onto cold water and made alkaline (pH=9) with solid K2CO3. The aqueous solution was extracted with Et2O (3×250 mL) and the separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, petroleum ether:EtOAc 95:5) affording the title compound (3.47 g, 15.46 mmol).

Aufarbeitung

  1. temperatureto cool to RT
  2. extractionThe aqueous solution was extracted with Et2O (3×250 mL)
  3. dry with materialthe separated organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, petroleum ether:EtOAc 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-ea912622638f403596548aa4bad79d7d
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729098B2

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