Benzyl Bromide → Methyl 4-benzyloxy-3-nitrobenzoate

HRID 1660803

Reaktionsgleichung

Reaktionsgleichung von HRID 1660803
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

Produkt 1

HCID 289857Methyl 4-benzyloxy-3-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 4-hydroxy-3-nitro-benzoic acid methyl ester (30 g, 152 mmol) in acetone (1000 mL) was charged into a 2 L reactor and treated with K2CO3 (31.5 g, 228 mol) and benzyl bromide (52 g, 36.1 mL, 304 mmol). The mixture was mechanically stirred at heated at reflux for 16 hours under a light argon flux. After cooling to room temperature the solvent was evaporated. The residue was taken up in ethyl acetate/water and the two phases were separated. The aqueous phase was extracted three times with ethyl acetate (total solvent volume: 1.5 L, total water volume 1 L). The combined organic phases were dried over sodium sulfate and evaporated. 4-Benzyloxy-3-nitro-benzoic acid methyl ester thus obtained was used crude in the following reaction.

Aufarbeitung

  1. temperatureat heated
  2. temperatureat reflux for 16 hours under a light argon flux
  3. customwas evaporated
  4. customthe two phases were separated
  5. extractionThe aqueous phase was extracted three times with ethyl acetate (total solvent volume: 1.5 L, total water volume 1 L)
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7cddeaed8130442db8fbd55c3661e0c9
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030308B2

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