Methanol → 2-(4-Nitrophenyl)butanol

HRID 1074442

Reaktionsgleichung

Reaktionsgleichung von HRID 1074442
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:14][CH3:15])[C:11](O)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:14][CH3:15])[CH2:11][OH:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 887MethanolHCID 240472-(4-Nitrophenyl)butyric acid

Produkt 1

HCID 204966922-(4-Nitrophenyl)butanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 20.9 g of 2-(4-nitrophenyl)butyric acid in 500 ml of dry tetrahydrofuran was added, dropwise, 1.1 equivalents of 10 M borane-dimethylsulfide complex in 100 ml of dry tetrahydrofuran. The mixture was stirred at room temperature for 1.5 hours and then refluxed for 1.5 hours and finally cooled to room temperature. Methanol (10 ml) was added, the mixture was stirred for 30 minutes, and the solvent was then evaporated under reduced pressure. The residue was dissolved in 100 ml of methanol and the solvent was evaporated and this procedure was repeated three (3) times. The resulting oil was purified by chromatography on silica gel, eluting with 1:1 ethyl acetate/hexane to give 2-(4-nitrophenyl)butanol as a light-yellow oil.

Aufarbeitung

  1. temperaturerefluxed for 1.5 hours
  2. temperaturefinally cooled to room temperature
  3. stirringthe mixture was stirred for 30 minutes
  4. customthe solvent was then evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 100 ml of methanol
  6. customthe solvent was evaporated
  7. customThe resulting oil was purified by chromatography on silica gel
  8. washeluting with 1:1 ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b7075177e6024583b3104666f58b59d3
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04391818

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