Hydrogen Peroxide → 3-(Benzyloxy)-4-methoxyphenol

HRID 1265152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1265152
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.S(=O)(=O)(O)[OH:22]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 806713-Benzyloxy-4-methoxybenzaldehyde

Produkt 1

HCID 135310983-(Benzyloxy)-4-methoxyphenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (0° C.), stirred solution of 3-benzyloxy-4-methoxybenzaldehyde (10 g) in MeOH (100 mL) was added hydrogen peroxide (5.5 mL of 30% aqueous) dropwise. After having been warmed to RT, concentrated sulfuric acid (1 mL) was added and the resulting solution was allowed to stir for 1.5 h. The reaction mixture was partitioned between ethyl ether/saturated aqueous sodium bicarbonate, another organic layer was dried over sodium sulfate and concentrated in vacuo to afford an oil. Flash chromatography (20% ethyl acetate/hexanes) afforded 3-benzyloxy-4-methoxyphenol (5.8 g).

Aufarbeitung

  1. temperatureAfter having been warmed to RT
  2. customThe reaction mixture was partitioned between ethyl ether/saturated aqueous sodium bicarbonate
  3. dry with materialanother organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford an oil

Quellen und Nachweise

ORD-Eintrag
ord-7066df0bbf2449cd9049779d00cc2059
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06545018B2

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