Nitroethane → 3-Nitro-1-phenoxy-butan-2-ol

HRID 13076

Reaktionsgleichung

Reaktionsgleichung von HRID 13076
[O:1]([CH2:8][CH:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].C(N1CCN2CCN(C(C)C)P1N(C(C)C)CC2)(C)C.[N+:37]([CH2:40][CH3:41])([O-:39])=[O:38]>[N+](C)([O-])=O>[N+:37]([CH:40]([CH3:41])[CH:9]([OH:10])[CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O-:39])=[O:38]

Komponenten

6

Edukt 4

HCID 6587NitroethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 75033PhenoxyacetaldehydeHCID 51483222,8,9-Triisopropyl-2,5,8,9-tetraaza-1-phosphabicyclo[3,3,3]undecane

Produkt 1

HCID 151053083-Nitro-1-phenoxy-butan-2-olAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6375NitromethaneLösungsmittel

Versuchsvorschrift

2-Phenoxyacetaldehyde (1.36 g, 10 mmol) was added to a suspension of anhydrous magnesium sulfate (2.65 g, 22 mmol) in nitroethane (7.0 mL) under an argon atmosphere. After 5 min a solution of 2,8,9-triisopropyl-2,5,8,9-tetraaza-1-phosphabicyclo[3,3,3]undecane (0.30 g, 1.0 mmol) in nitromethane (3.0 mL) was added. The mixture was vigorously stirred for 5 days at r.t., filtered through celite and concentrated. Purification by column chromatography (SiO2, dichloromethane/t-butyl methyl ether) gave the subtitle compound as an oil (1.7 g, 81%).

Aufarbeitung

  1. filtrationfiltered through celite and
  2. concentrationconcentrated
  3. customPurification by column chromatography (SiO2, dichloromethane/t-butyl methyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-fe19162b385a4d96923b629a75311512
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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