Ethanol → 4-(2,4-Dihydroxyphenyl)cyclohexanone Oxime

HRID 585687

Reaktionsgleichung

Reaktionsgleichung von HRID 585687
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.C(O)C.Cl.[NH2:20][OH:21]>C(N(CC)CC)C>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][C:12](=[N:20][OH:21])[CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 99424894-(2,4-Dihydroxyphenyl)cyclohexanone

Produkt 1

HCID 121351754-(2,4-Dihydroxyphenyl)cyclohexanone OximeAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a round bottomed flask, equipped with magnetic stirrer was added 4-(2,4-dihydroxyphenyl)cyclohexanone (100 mg, 0.49 mmol), anhydrous ethanol (5 ml), triethylamine (102 ml) and hydroxylamine hydrochloride (51 mg, 0.73 mmol). The reaction mixture was heated under reflux for 3 hr, then evaporated in vacuo. The resulting solid was purified by flash column chromatography, (SiO2, ethyl acetate/petroleum ether, 35:65, v/v), furnishing the title compound as short white needles (107 mg, 100%). δH (CD3OD) 1.44-1.61 (2H, m), 1.81-1.88 (1H, m), 1.94-2.00 (2H, m), 2.19-2.27 (1H, m), 2.43 (1H, d), 3.04-3.10 (1H, m), 3.38 (1H, m), 6.22-6.25 (1H, m), 6.28 (1H, d), 6.84-6.86 (1H, m); m/z (EI−) 220.

Aufarbeitung

  1. customTo a round bottomed flask, equipped with magnetic stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 3 hr
  4. customevaporated in vacuo
  5. customThe resulting solid was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8739394824ee4593a6aab73a44d4e366
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933319B2

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