Triphenylphosphine → 3-(3-Hydroxy-4-methoxyphenyl)propanal

HRID 1007624

Reaktionsgleichung

Reaktionsgleichung von HRID 1007624
[H][H].[OH:3][C:4]1[CH:5]=[C:6]([CH2:12][CH2:13][C:14](O)=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].C(OC(=O)C(C)(C)C)(=O)C(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1>[OH:3][C:4]1[CH:5]=[C:6]([CH2:12][CH2:13][CH:14]=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 15234Pivalic anhydrideHCID 27520543-Hydroxy-4-methoxybenzenepropanoic acidHCID 178418361HCID 178418361, Verbindung3×

Produkt 1

HCID 98154073-(3-Hydroxy-4-methoxyphenyl)propanalAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Into a chemical reactor for hydrogen addition (hydrogenation) under elevated pressure, 3-(3-hydroxy-4-methoxyphenyl) propionic acid (5.09 g, 25.9 mmol), pivalic acid anhydride (14.3 g, 76.6 mmol), and tetrahydrofuran (64 ml) were added, and thereafter the mixture was bubbled with nitrogen gas for 10 minutes. Palladium acetate (57 mg, 0.254 mmol) and triphenylphosphine (349 mg, 1.33 mmol) were added thereto, and thereafter the mixture was bubbled with nitrogen gas for 20 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 5.4 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: hexane/ethyl acetate=2/1). The thus eluted fractions containing the object compound were concentrated under reduced pressure to obtain crude 3-(3-hydroxy-4-methoxyphenyl) propionaldehyde (2.26 g, 12.5 mmol, yield: 48%) in the slightly yellow coloured solid.

Aufarbeitung

  1. additionwere added
  2. customthe mixture was bubbled with nitrogen gas for 10 minutes
  3. customthe mixture was bubbled with nitrogen gas for 20 minutes
  4. customin the system of reaction, whereby the system
  5. additionwas filled with nitrogen gas
  6. customfor reaction
  7. customThus obtained reaction solution
  8. concentrationwas concentrated under reduced pressure
  9. customto remove tetrahydrofuran by vaporization
  10. washThe remaining residue was subjected to a purification process with a silica gel column chromatography (eluting solvent: hexane/ethyl acetate=2/1)
  11. additionThe thus eluted fractions containing the object compound
  12. concentrationwere concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dd92e597e4f44b2c8659e4a504ec2880
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794531B2

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