3-Methoxybenzaldehyde → HCID 20523216, Verbindung

HRID 127921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 127921
[CH3:1]OC1C=C(C=CC=1)C=O.COC(OC)CN.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=1)[CH:23]=[N:24][CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28].C[Mg]I>CCOCC.O.C1(C)C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=1)[CH:23]([NH:24][CH2:25][CH:26]([O:27][CH3:28])[O:29][CH3:30])[CH3:1]

Komponenten

8

Edukt 4

HCID 115693-MethoxybenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 1315411839964-84-6HCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 20523216HCID 20523216, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 13.6 g. (0.1 mole) of 3-methoxy-benzaldehyde and 10.5 g. (0.1 mole) of aminoacetaldehyde dimethyl acetal in 250 ml. of toluene is refluxed for one hour and water produced in the reaction is collected in a Dean-Stark trap. The resulting solution of 3-methoxy-N-(2,2-dimethoxyethyl)benzylidenamine is added to a solution of (0.2 mole) of methylmagnesium iodide in 250 ml. of ether over 1.5 hours. The mixture is stirred for one hour, cooled and quenched by careful addition of 250 ml. of water. The aqueous phase was filtered through Celite, extracted with 150 ml. of ether and the combined organic phases washed, dried and evaporated to yield 3-methoxy-α-methyl-N-(2,2-dimethoxyethyl)benzylamine.

Aufarbeitung

  1. customis collected in a Dean-Stark trap
  2. temperaturecooled
  3. customquenched by careful addition of 250 ml
  4. filtrationThe aqueous phase was filtered through Celite
  5. extractionextracted with 150 ml
  6. washof ether and the combined organic phases washed
  7. customdried
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f367050b0fa64c8f82d267e45b77aa7b
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04258049

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