Eugenol → 4-Propylguaiacol

HRID 1635789

Reaktionsgleichung

Reaktionsgleichung von HRID 1635789
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1)[CH:2]=[CH2:3].C1(C)C=CC(S(NN)(=O)=O)=CC=1.CC([O-])=O.[Na+]>C(COC)OC.O>[CH3:12][O:11][C:6]1[CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[CH:9]=[CH:8][C:7]=1[OH:10]

Komponenten

6

Edukt 3

HCID 3314EugenolHCID 15303P-ToluenesulfonylhydrazideHCID 517045Sodium Acetate

Produkt 1

HCID 177394-PropylguaiacolAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of 123 mg (0.75 mmole) of 4-allyl-2-methoxyphenol (eugenol) and 1.4 gm (7.5 mmole)of p-toluenesulfonhydrazide in 15 ml of dimethoxyethane under reflex was added a solution of 1.7 gm of NaOAc in 15 ml water over a 4 hour period. The mixture was cooled to room temperature, poured into 20 ml of water, and extracted three times with 30 ml of CH2Cl2. The combined organic layers were washed with 50 ml of water, dried over MgSO4, and concentrated under vacuo. The resulting solid was flash chromatographed over silica gel using 10% ethyl acetate in hexane to afford 60 mg of 2-methoxy-4-propylphenol in 48% yield.

Aufarbeitung

  1. extractionextracted three times with 30 ml of CH2Cl2
  2. washThe combined organic layers were washed with 50 ml of water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuo
  5. customchromatographed over silica gel using 10% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-2f4fba126928419f8728e7e159f2c18d
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06511966B2

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