Water → 2-Chlorocinnamaldehyde

HRID 537392

Reaktionsgleichung

Reaktionsgleichung von HRID 537392
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH2:9]([OH:12])[CH:10]=[CH2:11].C([O-])(O)=O.[Na+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:11]=[CH:10][CH:9]=[O:12]

Komponenten

8

Edukt 4

HCID 962WaterHCID 7858Allyl AlcoholHCID 119931-Chloro-2-iodobenzeneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 30140422-ChlorocinnamaldehydeAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A mixture of 2.2 mL (18 mmol) of 2-chloroiodobenzene, 1.8 mL (27 mmol) of allyl alcohol, 81 mg (0.36 mmol) of Pd(OAc)2, 5.3 g (18 mmol) of Bu4NCl, and 3.8 g (45 mmol) of NaHCO3 in 50 mL of DMF is stirred under Ar2 at 30° C. for 24 h. Water is added and the mixture is extracted with EtOAc. The extract is washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (0-50% EtOAc in hexanes) provides 2.2 g (74%) of 3-(2-chlorophenyl)propenal.

Aufarbeitung

  1. extractionthe mixture is extracted with EtOAc
  2. washThe extract is washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6790add3008d4712b95d944557dca659
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859814B2

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