Acetic Acid → HCID 54218658, Verbindung

HRID 1981475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1981475
[H-].[Na+].[CH3:3][N:4]([CH3:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[H][H].C(O)(=O)C.[C:20]([O:23][CH:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:25])(=[O:22])[CH3:21]>O>[CH3:3][N:4]([CH3:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:21][C:20]([O:23][CH:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:25])=[O:22])=[CH:7][CH:6]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 24758Sodium hydrideHCID 979871-Methylheptyl acetateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 54218658HCID 54218658, VerbindungAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydride (1.9 g of an 80% dispersion in oil) was added portionwise with stirring over 0.5 hour to 4-dimethylaminobenzaldehyde (7.46 g) in 2-octyl acetate (153 g) at 25° C. The temperature was raised until a steady evolution of hydrogen began (100° C.) and held at this temperature for eight hours. The cooled mixture was treated with glacial acetic acid (4 ml) and then water (50 ml) added. The upper layer was separated, washed with 10% sodium carbonate solution, water, and dried (MgSO4). The excess of 2-octyl acetate was removed by distillation at 15 mm pressure, and the residue fractionated under high vacuum, yielding 7.3 g 2-octyl 4-dimethylaminocinnamate as a pale amber viscous oil, b.p. 194°-200° C./0.25 mm. After freezing it remelted at -11° C.

Aufarbeitung

  1. custom(100° C.)
  2. customThe upper layer was separated
  3. washwashed with 10% sodium carbonate solution, water
  4. dry with materialdried (MgSO4)
  5. customThe excess of 2-octyl acetate was removed by distillation at 15 mm pressure

Quellen und Nachweise

ORD-Eintrag
ord-1dff30d49fc249c89ffe36666328ccd4
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04592906

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