Acetic Acid → 2-Ethylhexyl 3-(4-aminophenyl)-2-cyanoacrylate

HRID 133687

Reaktionsgleichung

Reaktionsgleichung von HRID 133687
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH2:12][C:13]([O:15][CH2:16][CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])=[O:14])#[N:11].C(NCC)C.C(O)(=O)C>C(O)(C)C>[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:12]([C:10]#[N:11])[C:13]([O:15][CH2:16][CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])=[O:14])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8021DiethylamineHCID 111584-AminobenzaldehydeHCID 963592-Ethylhexyl cyanoacetate

Produkt 1

HCID 538516112-Ethylhexyl 3-(4-aminophenyl)-2-cyanoacrylateAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

36.3 g (0.3 mol) of p-aminobenzaldehyde are suspended in 450 ml of isopropanol. A mixture of 59.1 g (0.3 mol) of 2-ethylhexyl cyanoacetate and of catalyst (0.375 ml of diethylamine and 1.125 ml of acetic acid) is introduced therein. The mixture is refluxed for 5 hours. The same amount of catalyst is added again and refluxing is continued for a further 4 hours. The insoluble materials are removed by hot filtration and the mixture is concentrated to a volume of 300 ml and left to crystalize. After filtration and drying, 59.6 g (66% yield) of an orange-coloured powder are obtained, and are used without further purification for the following step.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 5 hours
  2. additionThe same amount of catalyst is added again
  3. temperaturerefluxing
  4. customThe insoluble materials are removed by hot filtration
  5. concentrationthe mixture is concentrated to a volume of 300 ml
  6. waitleft
  7. customto crystalize
  8. filtrationAfter filtration
  9. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-241a139bf82a4c8981d30fdba0222782
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390916B2

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