Cornforth reagent → 5-Methoxy-2-nitrobenzaldehyde

HRID 525421

Reaktionsgleichung

Reaktionsgleichung von HRID 525421
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH2:9][OH:10])[CH:8]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:8]=1)[CH:9]=[O:10]

Komponenten

4

Edukt 2

HCID 2724130Cornforth reagentHCID 53405061(5-Methoxy-2-nitrophenyl)methanol

Produkt 1

HCID 2303715-Methoxy-2-nitrobenzaldehydeAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the solution of (5-methoxy-2-nitrophenyl)methanol (18 g, 0.098 mol) in anhydrous DCM (0.2 L) was added PDC (11.5 g, 0.147 mol, 1.5 eq) and 4 A MS (120 g) in portions. The mixture was stirred at room temperature for 16 h, filtered through a Celite pad. The filtrate was evaporated to dryness in vacuum to afford 5-methoxy-2-nitrobenzaldehyde (10 g, yield: 57%) as a light yellow solid. 1HNMR (400 MHz, DMSO-d6) δ: 10.24 (s, 1H), 8.14 (d, J=8.8 Hz, 1H), 7.31 (dd, J=8.8, 3.2 Hz, 1H), 7.20 (d, J=3.2 Hz, 1H), 3.89 (s, 3H); ESI-MS: m/z 182.0 ([M+1]+).

Aufarbeitung

  1. filtrationfiltered through a Celite pad
  2. customThe filtrate was evaporated to dryness in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-97523c4ee3394e04824e85acaa4a7047
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340527B2

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