Hydrochloric Acid → 3-(3-Nitrophenyl)propan-1-ol

HRID 1093497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1093497
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12](O)=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].O1CCCC1.B.O.Cl>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 27602243-(3-Nitrophenyl)propionic acid

Produkt 1

HCID 113328423-(3-Nitrophenyl)propan-1-olAusbeute 23,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3-(3-Nitrophenyl)propionic acid (1.00 g) was dissolved in tetrahydrofuran (20 ml), and a tetrahydrofuran-borane.tetrahydrofuran solution (1 mol/l, 7.25 ml) was added dropwise to the mixture under ice-cooling. The mixture was stirred under ice-cooling for 30 min, and further at room temperature for 2.5 hr. Water was added to the reaction mixture, and 1 mol/1 aqueous hydrochloric acid solution was added. The mixture was extracted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give the object product (220 mg) as a yellow oil.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling for 30 min
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-be630578ab42463ba2b5f903c116a71c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129361B2

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