3-Nitrosalicylic acid → 2-Benzyloxy-3-nitro-benzoic Acid Benzyl Ester

HRID 1064840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064840
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]=1[OH:19])([O-:9])=[O:8].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.O>[CH2:20]([O:19][C:11]1[C:10]([N+:7]([O-:9])=[O:8])=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH2:13][C:12]1[CH:16]=[CH:17][CH:18]=[CH:10][CH:11]=1)=[O:14])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 3

HCID 68073-Nitrosalicylic acidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Produkt 1

HCID 161066762-Benzyloxy-3-nitro-benzoic Acid Benzyl EsterAusbeute 162,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Potassium carbonate (16.6 g, 120.1 mmol) was added to a solution of 3-nitrosalicylic acid (10 g, 54.6 mmol) in DMF (100 ml) and benzyl bromide (14.3 ml, 120.1 mmol) was dropped thereinto. The mixture was stirred at 80° C. for 12 hours and the reaction solution was diluted with water and extracted with ether. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and the solvent was evaporated therefrom to provide 16.1 g (yield 81%) of benzyl 2-benzyloxy-3-nitrobenzoate as brown oil.

Aufarbeitung

  1. additionwas dropped
  2. extractionextracted with ether
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-76696d917e2a459a86cc68998cf3ba90
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969711B2

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