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

HRID 913323

Reaktionsgleichung

Reaktionsgleichung von HRID 913323
[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-diethoxybenzaldehydeAusbeute 88,2 %

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 was extracted with ethyl acetate (3×50 mL), and the combined organic phase was washed with water, dried over MgSO4 and evaporated to dryness providing thereby 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 was extracted with ethyl acetate (3×50 mL)
  3. washthe combined organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customproviding

Quellen und Nachweise

ORD-Eintrag
ord-fa417d7b9c2c4f9193a24ba7efd6bfad
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026365B2

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