Pivalic anhydride → 3-(3-Hydroxy-4-methoxyphenyl)prop-2-enal

HRID 1007621

Reaktionsgleichung

Reaktionsgleichung von HRID 1007621
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:5]=[CH:6][C:7](O)=[O:8].C(OC(=O)C(C)(C)C)(=O)C(C)(C)C.[H][H]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC(P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:5]=[CH:6][CH:7]=[O:8]

Komponenten

6

Edukt 3

HCID 15234Pivalic anhydrideHCID 921263-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acidHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 540251573-(3-Hydroxy-4-methoxyphenyl)prop-2-enalAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 13956Phosphine, tris(4-methylphenyl)-KatalysatorHCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Palladium acetate (58 mg, 0.257 mmol), tri(p-tolyl) phosphine (157 mg, 0.515 mmol), 3-hydroxy-4-methoxycinnamic acid (5.00 g, 25.7 mmol) and pivalic acid anhydride (14.4 g, 77.2 mmol) were added thereto, and thereafter the mixture was bubbled with nitrogen gas for 30 minutes to substitute nitrogen gas completely for the gas in the system of reaction, whereby the system was filled with nitrogen gas. Next, hydrogen gas was added thereinto to substitute hydrogen gas for the gas in the system, and then the mixture was stirred under hydrogen pressure of 3.4 MPa at 80° C. for 24 hours for reaction. Thus obtained reaction solution was concentrated under reduced pressure to remove tetrahydrofuran by vaporization. The remaining residue was subjected to a purification process with a silica gel column chromatography (eluting solvent: toluene/ethyl acetate=4/1) to obtain 3-hydroxy-4-methoxycinnamaldehyde (2.26 g, 12.7 mmol, yield: 49%).

Aufarbeitung

  1. customthe mixture was bubbled with nitrogen gas for 30 minutes
  2. customin the system of reaction, whereby the system
  3. additionwas filled with nitrogen gas
  4. customfor reaction
  5. customThus obtained reaction solution
  6. concentrationwas concentrated under reduced pressure
  7. customto remove tetrahydrofuran by vaporization
  8. washThe remaining residue was subjected to a purification process with a silica gel column chromatography (eluting solvent: toluene/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-5fbb8291ec95476a9ec895955de679cc
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794531B2

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