Tyrosol → 4-Hydroxyphenylacetaldehyde

HRID 37763

Reaktionsgleichung

Reaktionsgleichung von HRID 37763
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C1C=CN=CC=1.O=S(=O)=O>CS(C)=O.C(Cl)Cl>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH:7]=[O:8])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 10393TyrosolHCID 168533Sulfur trioxide-pyridine

Produkt 1

HCID 4401134-HydroxyphenylacetaldehydeAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-hydroxyphenylacetaldehyde (15) was synthesized as described in Heterocycles, 2000, 53, 777-784. 4-Hydroxyphenethyl alcohol (Compound 141.0 g, 7.3 mmol, Aldrich) was dissolved in dimethylsulfoxide (8 mL, Aldrich). With stirring, TEA (2.2 mL, 16 mmol, Aldrich) was added slowly. Pyridine-sulfur trioxide (SO3.py) complex (2.5 g, 16 mmol, Aldrich) was completely dissolved in dimethylsulfoxide (9 mL, Aldrich) and this solution was added drop-wise to the alcohol, with vigorous stirring. After stirring for 1 h at room temperature, the reaction was diluted with CH2Cl2, then washed with ice-cold water. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness. Purification using silica gel chromatography with hexane-ethyl acetate as eluent (5:1, then 2:1) yielded 488 mg (49%) of 4-hydroxyphenylacetaldehyde (15).

Aufarbeitung

  1. custom4-hydroxyphenylacetaldehyde (15) was synthesized
  2. stirringAfter stirring for 1 h at room temperature
  3. washwashed with ice-cold water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-52d55c87f4e34d32b565dac39979b5e0
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524660B2

Verknüpfte Notizen

Wird geladen…