Acrylic Acid → HCID 131734706, Verbindung

HRID 1773127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773127
[C:1]([O:4][C:5]1[CH:12]=[CH:11][C:10](I)=[CH:9][C:6]=1[CH:7]=[O:8])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:21]([OH:25])(=[O:24])[CH:22]=[CH2:23].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:7]([C:6]1[CH:9]=[C:10]([CH:11]=[CH:12][C:5]=1[O:4][C:1](=[O:3])[CH3:2])[CH:23]=[CH:22][C:21]([OH:25])=[O:24])=[O:8]

Komponenten

7

Edukt 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 89690163HCID 89690163, Verbindung

Produkt 1

HCID 131734706HCID 131734706, VerbindungAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
67.5 °C

Versuchsvorschrift

2-Acetyloxy-5-iodobenzaldehyde (0.2 g, 0.69 mmol) is dissolved in 25 ml of acetonitrile and oxygen is removed by bubbling nitrogen through the solution. Triethylamine (0.673 ml, 4.82 mmol) and acrylic acid (0.095 ml, 1.38 mmol) are added dropwise with stirring, followed by 0.016 g of tri-o-tolylphosphine (0.069 mmol) and 0.008 of palladium(II) acetate (0.047 mmol). The mixture is heated at 65-70° C. for 4 hours, volatiles are removed by distillation and the residue is purified by column chromatography on silica gel, eluting with mixtures of ethyl acetate-hexane of increasing polarity. 3-Formyl-4-acetyloxycinnamic acid (0.095 g) is obtained as a white solid.

Aufarbeitung

  1. customoxygen is removed
  2. customby bubbling nitrogen through the solution
  3. customvolatiles are removed by distillation
  4. customthe residue is purified by column chromatography on silica gel
  5. washeluting with mixtures of ethyl acetate-hexane
  6. temperatureof increasing polarity

Quellen und Nachweise

ORD-Eintrag
ord-5390f510b97446bf9fdb0bed01d6f9b5
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255071B2

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