1-Butanol → 5-Butoxy-2-nitrobenzoic acid methyl ester

HRID 72197

Reaktionsgleichung

Reaktionsgleichung von HRID 72197
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][CH3:6].C(=O)=O.[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[C:18](F)[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[C:18]([O:7][CH2:3][CH2:4][CH2:5][CH3:6])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]

Komponenten

7

Edukt 4

HCID 2631-ButanolHCID 280Carbon DioxideHCID 24758Sodium hydrideHCID 51520495-Fluoro-2-nitrobenzoic acid methyl ester

Produkt 1

HCID 689764995-Butoxy-2-nitrobenzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (302.4 mg) was added to a solution of 1-butanol (0.634 mL) in DMF (15 mL). The reaction mixture was stirred until there was no further evolution of CO2 and then 5-fluoro-2-nitrobenzoic acid methyl ester (1.15 g) was added and the mixture was stirred at room temperature overnight. The reaction was then mixed with ethyl acetate, washed with 10% sodium bicarbonate and 10% citric acid solution, dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC. The product with the molecular weight of 253.26 (C12H15NO5) was obtained in this way; MS (ESI): 254 (M+H+).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. washwashed with 10% sodium bicarbonate and 10% citric acid solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC
  6. customThe product with the molecular weight of 253.26 (C12H15NO5) was obtained in this way

Quellen und Nachweise

ORD-Eintrag
ord-bb61bd3967b346ddbd2607904150f60b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828991B2

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