[2-(Propan-2-ylamino)phenyl]methanol → 2-((Propan-2-yl)amino)benzaldehyde

HRID 12375

Reaktionsgleichung

Reaktionsgleichung von HRID 12375
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][OH:12])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=[O:12])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 10797123[2-(Propan-2-ylamino)phenyl]methanol

Produkt 1

HCID 110410352-((Propan-2-yl)amino)benzaldehydeAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
117 °C

Versuchsvorschrift

Manganese dioxide (85% 182.6 g, 1.79 mol) was added to a stirred solution of 2-isopropylaminophenylmethanol (118 g, 0.71 mol) in toluene (800 mL) and the reaction mixture was heated to 117° C. for 4 h. The reaction mixture was allowed to cool to room temperature overnight and then filtered through a pad of Celite which was eluted with toluene. The filtrate was concentrated under reduced pressure to yield 2-isopropylaminobenzaldehyde (105 g, 90%) as an orange oil. 1H NMR (CDCl3; 300 MHz): 1.28 (d, 6H, CH(CH3)2), 3.76 (sept, 1H, CH(CH3)2), 6.65 (t, 1H, ArH), 6.69 (d, 1H, ArH), 7.37 (d, 1H, ArH), 7.44 (t, 1H, ArH), 9.79 (s, 1H, CHO).

Aufarbeitung

  1. temperatureto cool to room temperature overnight
  2. filtrationfiltered through a pad of Celite which
  3. washwas eluted with toluene
  4. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0b646f22560f477fb1da598dcb7191c5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728006B2

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