Nitric Acid → 5,6,7,8-Tetrahydro-1-nitro-2-naphthalenol

HRID 2393297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393297
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].CCOCC.[N+:17]([O-])([OH:19])=[O:18]>O>[OH:11][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:1]=1[N+:17]([O-:19])=[O:18]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 143055,6,7,8-Tetrahydro-2-naphthol

Produkt 1

HCID 49137365,6,7,8-Tetrahydro-1-nitro-2-naphthalenolAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5,6,7,8-Tetrahydro-2-naphthol (50 g, 0.337 mol) was mixed with ether (400 ml), and the mixture was added dropwise with 60% nitric acid (28 ml, 0.368 mol) while the reaction temperature was kept below 15° C. , and then stirring was continued at 15° to 20° C. for 1 hour. The reaction mixture was added with water (500 ml) and extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated. The residue was purified by silica gel chromatography (Wako Gell C-300: 900 g, eluent: hexane/ethyl acetate=50/1 to 60/1) to give 2-hydroxy-5,6,7,8-tetrahydro-1-nitronaphthalene (21.2 g).

Aufarbeitung

  1. customwas kept below 15° C.
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel chromatography (Wako Gell C-300: 900 g, eluent: hexane/ethyl acetate=50/1 to 60/1)

Quellen und Nachweise

ORD-Eintrag
ord-e5b36d05147d4a7fa702566fb88c1532
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807860

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