Nitric Acid → 1-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

HRID 15512

Reaktionsgleichung

Reaktionsgleichung von HRID 15512
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:20]([O-])([OH:22])=[O:21].OS(O)(=O)=O.O>ClCCl>[CH2:1]([O:8][C:9]1[C:10]([O:18][CH3:19])=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[C:13]([N+:20]([O-:22])=[O:21])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 944Nitric Acid2×HCID 962WaterHCID 1118Sulfuric AcidHCID 992151-(4-Benzyloxy-3-methoxy-phenyl)-ethanone

Produkt 1

HCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanoneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(4-(benzyloxy)-3-methoxyphenyl)ethanone (5.0 g, 19.5 mmol, Alfa Aesar Company) in dichloromethane (75 mL) at ice bath temp. was added slowly HNO3 (1.5 mL of 90% nitric acid) followed by conc H2SO4 (1.8 mL of 96.2% acid) at 0° C. with stirring. After 1 h at 0° C. additional HNO3 (0.5 mL) was added and the reaction mixture was stirred for 20 minutes at 0° C. To the reaction mixture was added dichloromethane (25 mL) and the mixture was poured into water (60 mL), the organic layer was separated which was washed with water (2×60 mL) followed by aq NaHCO3 (2×60 mL), dried over Na2SO4 and concentrated in vacuo. The residue was mixed with DMF (˜3 mL) and ether (70 mL), stirred for a while and the solid was filtered, washed with a small amount of ether and dried to obtain the desired product (3.6 g, 61%) as a yellow solid. 1H NMR (CDCl3) δ 7.64 (s, 1H), 7.42-7.35 (m, 5H), 6.76 (s, 1H), 5.21 (s, 2H), 3.93 (s, 3H), 2.48 (s, 3H).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 20 minutes at 0° C
  2. customthe organic layer was separated which
  3. washwas washed with water (2×60 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. additionThe residue was mixed with DMF (˜3 mL) and ether (70 mL)
  7. stirringstirred for a while
  8. filtrationthe solid was filtered
  9. washwashed with a small amount of ether
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-68309dd712e84741adb6875dc4eccaa7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732613B2

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