Water → Methyl 4-methoxy-2-nitrobenzoate

HRID 1672175

Reaktionsgleichung

Reaktionsgleichung von HRID 1672175
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[CH2:15]1CCN2C(=NCCC2)CC1.IC.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:15])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2886574-Methoxy-2-nitrobenzoic acid

Produkt 1

HCID 17733355Methyl 4-methoxy-2-nitrobenzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-methoxy-2-nitrobenzoic acid (10.0 g, 50.7 mmol) in DMF (200 mL) at 0° C. was added DBU (15.2 mL, 101 mmol) followed by iodomethane (9.47 mL, 152 mmol). The reaction mixture was allowed to stir at 0° C. for 15 min then at rt overnight. The mixture was poured into water and extracted with EtOAc. The organic solutions were combined, washed with brine and dried over MgSO4. The residue was purified by column chromatography to give methyl 4-methoxy-2-nitrobenzoate (50.7 mmol, 85%) as a yellow solid. LCMS (FA): m/z=212.1 (M+H).

Aufarbeitung

  1. customat rt
  2. customovernight
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-010c35de66744815b55ad6a308a4d58e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998952B2

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