Sodium Carbonate → 4-Methoxy-3,5-dimethylbenzaldehyde oxime

HRID 387210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387210
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[CH3:12].Cl.[NH2:14][OH:15].C([O-])([O-])=O.[Na+].[Na+]>C(O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:6]([CH:7]=[N:14][OH:15])=[CH:5][C:4]=1[CH3:12]

Komponenten

6

Edukt 3

HCID 10340Sodium Carbonate2×HCID 443297Hydroxyamine hydrochloride2×HCID 27585734-Methoxy-3,5-dimethylbenzaldehyde

Produkt 1

HCID 724690044-Methoxy-3,5-dimethylbenzaldehyde oxime

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-Methoxy-3,5-dimethylbenzaldehyde (1.86 g, 11.3 mmol) was dissolved in ethanol (30 mL) and stirred with hydroxylamine hydrochloride (2.4 M aq. solution, 5.65 mL, 1.2 eq.) and Na2CO3 (1.2 M solution, 5.65 mL, 0.6 eq.) at room temperature for 2.5 hours. The mixture was then heated to 60° C. and additional hydroxylamine hydrochloride and Na2CO3 was added. The mixture was again stirred overnight at 60° C., transferred to a separatory funnel, diluted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated. The product was purified by ISCO chromatography with EtOAc/hexanes eluent to yield 1.55 g (8.56 mmol) of 4-methoxy-3,5-dimethylbenzaldehyde oxime as a white solid. M+1=180.0.

Aufarbeitung

  1. customtransferred to a separatory funnel
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by ISCO chromatography with EtOAc/hexanes eluent

Quellen und Nachweise

ORD-Eintrag
ord-28cffe0bb3e540ceb998a784dd97a039
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372873B2

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