Water → 2-(2,4-Dinitrophenyl)ethanol

HRID 511704

Reaktionsgleichung

Reaktionsgleichung von HRID 511704
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14](O)=[O:15])([O-:3])=[O:2].O.CCCCCC>O1CCCC1>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH2:14][OH:15])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8058HexaneHCID 2215132,4-Dinitrophenylacetic acid

Produkt 1

HCID 118307342-(2,4-Dinitrophenyl)ethanolAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

22.6 g (100 mmol) 2,4-dinitrophenylacetic acid is dissolved in 150 ml tetrahydrofuran and added dropwise in a the course of 2 hours to 300 ml (300 mmol) of a borane-tetrahydrofuran complex 1.0 M solution in tetrahydrofuran. After 3 hours at 25° C., 200 ml water is carefully added. The reaction mixture is then partitioned between ethyl acetate and water; the organic phase is washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 400 g silica gel using toluene:ethyl acetate 1:1 as eluant and crystallization form ethylacetate:hexane mixture to yield 20.7 g (98%) of 2-(2,4-dinitrophenyl)ethanol as yellowish crystals.

Aufarbeitung

  1. customThe reaction mixture is then partitioned between ethyl acetate and water
  2. washthe organic phase is washed repeatedly with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customcrystallization
  7. customform ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-be5cc25c3e764b5b996d74db58f746c8
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09097938B2

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