Sodium Hydroxide → HCID 86652761, Verbindung

HRID 453930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453930
[CH:1]1([O:6][C:7]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:18][OH:19].[OH-].[Na+]>C(O)C>[CH:1]1([O:6][C:7]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=[N:18][OH:19])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 6484666HCID 6484666, Verbindung

Produkt 1

HCID 86652761HCID 86652761, VerbindungAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To the stirred solution of 2-(cyclopentyloxy)-3-methoxybenzaldehyde (3 g, 13.636 mmol) in ethanol was added hydroxylamine hydrochloride (1.758 g, 27.277 mmol) and aqueous solution of sodium hydroxide (18 ml, 34.091 mmol). The reaction mixture was refluxed for 6 h under nitrogen atmosphere. The solvent was evaporated under reduced pressure and the reaction mixture diluted with water. The product was extracted using chloroform (3×200 ml), combined organic layers washed with water (3×100 ml), brine (50 ml), dried (Na2SO4), filtered and concentrated under vacuum to yield 3.12 g of the product. 1H NMR (300 MHz, CDCl3) δ 1.58-1.64 (m, 4H), 1.66-1.72 (m, 4H), 3.84 (s, 3H), 4.86 (br s, 1H), 6.89 (d, J=8.1 Hz, 1H), 6.99 (t, J=7.8 Hz, 1H), 7.31 (d, J=7.8 Hz, 1H), 8.43 (s, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 6 h under nitrogen atmosphere
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe reaction mixture diluted with water
  4. extractionThe product was extracted
  5. washwashed with water (3×100 ml), brine (50 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6d899aa9929c4ee39f4ebd274987225a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492568B2

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