Hydrochloric Acid → 2-Hydroxy-α-methyl-6-nitrobenzenemethanol

HRID 1767308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767308
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=[O:5].[CH3:13][Al](C)C.Cl>>[OH:5][CH:4]([C:3]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=1[OH:1])[CH3:13]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 109539092-Hydroxy-6-nitrobenzaldehydeHCID 16682925Trimethylaluminum

Produkt 1

HCID 222589412-Hydroxy-α-methyl-6-nitrobenzenemethanolAusbeute 95 %

Versuchsvorschrift

To a stirred solution of 2-hydroxy-6-nitrobenzaldehyde (4.5 g, 26.926 mmol) was added dropwise trimethylaluminum (2M in toluene, 27 mL) under an argon atmosphere. The mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into a cold (0° C.) aqueous 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1) to give 2-(1-hydroxyethyl)-3-nitrophenol as an orange oil (4.660 g, yield; 95%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-5f4cc75f9c284b578904989fa606f22d
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07232909B2

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