(4-Amino-3,5-diethoxy-phenyl)-methanol → 4-Amino-3,5-diethoxybenzaldehyde

HRID 547942

Reaktionsgleichung

Reaktionsgleichung von HRID 547942
[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]([CH2:11][OH:12])=[CH:4][C:3]=1[O:13][CH2:14][CH3:15]>CN(C=O)C.O=[Mn]=O>[NH2:1][C:2]1[C:3]([O:13][CH2:14][CH3:15])=[CH:4][C:5]([CH:11]=[O:12])=[CH:6][C:7]=1[O:8][CH2:9][CH3:10]

Komponenten

4

Edukt 1

HCID 66912271(4-Amino-3,5-diethoxy-phenyl)-methanol

Produkt 1

HCID 591282764-Amino-3,5-diethoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (4-amino-3,5-diethoxy-phenyl)-methanol (0.79 g, 3.74 mmol, 1.0 equiv) in DMF (20 mL) was added activated MnO2 (1.63 g, 18.70 mmol, 5.0 equiv). The reaction mixture was stirred for 24 h at rt, filtered through Hyflo Super Cel, the filtrate extracted with ethyl acetate (3×50 mL) and the combined organic phases dried over MgSO4 providing 0.69 g (88%) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.46 (t, J=7.0 Hz, 3H), 4.15 (q, J=7.0 Hz, 2H), 4.50 (br s, 2H), 7.04 (s, 2H), 9.70 (s, 1H). MS (ISP): 210.0 [M+H]+.

Aufarbeitung

  1. filtrationfiltered through Hyflo Super Cel
  2. extractionthe filtrate extracted with ethyl acetate (3×50 mL)
  3. dry with materialthe combined organic phases dried over MgSO4 providing 0.69 g (88%) of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-216c306af27846be91de39e035cdbbec
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939661B2

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