1-(4-Methoxyphenyl)ethanol → 4-Methoxyphenylacetaldehyde

HRID 221814

Reaktionsgleichung

Reaktionsgleichung von HRID 221814
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[CH3:10])=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:14]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]=[O:14])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 1011481-(4-Methoxyphenyl)ethanolHCID 159087Triacetoxyperiodinane

Produkt 1

HCID 797824-MethoxyphenylacetaldehydeAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-methoxyphenyl ethanol (15.0 g, 98.2 mmol) in 150 mL of methylene chloride was stirred at 0° C. while Dess-Martin periodinane (50 g, 1.2 eq.) was added in small portions. The ice-bath was removed and the reaction was stirred at rt for 1 h. The reaction mixture was then diluted with methylene chloride (100 mL), washed with 10% sodium thiosulfate, saturated NaHCO3 solution, water, saturated NaCl solution, and dried over Na2SO4. The product was purified using silica gel chromatography (100% hexanes to 20% EtOAC/hexanes) to afford 5.3 g (34%) of 4-methoxyphenyl acetaldehyde.

Aufarbeitung

  1. additionwas added in small portions
  2. customThe ice-bath was removed
  3. additionThe reaction mixture was then diluted with methylene chloride (100 mL)
  4. washwashed with 10% sodium thiosulfate, saturated NaHCO3 solution, water, saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. customThe product was purified

Quellen und Nachweise

ORD-Eintrag
ord-501fe0a586964996b9016fe34e351183
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207168B2

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