Veratrole → 4-(11-Cyanoundecanoyl)-1,2-dimethoxybenzene

HRID 2254336

Reaktionsgleichung

Reaktionsgleichung von HRID 2254336
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)#[N:2].ClCC(OC(=O)CCl)=O.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34]>ClC(Cl)C>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:30]1[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[C:28]([O:33][CH3:34])[CH:29]=1)=[O:15])#[N:2]

Komponenten

5

Edukt 3

HCID 7043VeratroleHCID 10946Chloroacetic anhydrideHCID 7987911-Cyanoundecanoic acid

Produkt 1

HCID 197452394-(11-Cyanoundecanoyl)-1,2-dimethoxybenzeneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

In 50 ml of dichloroethane were dissolved 10.5 g (0.05 mole) of 11-cyanoundecanoic acid and 10.26 g (0.06 mole) of monochloroacetic anhydride. To the resulting solution were added 8.98 g (0.065 mole) of 1,2-dimethoxybenzene and 0.71 g of boron trifluoridediethyl ether complex and the resulting mixture was then stirred at 75° C. for 6 hours. After completion of the reaction, the reaction solution was cooled and washed successively with water, 5% aqueous sodium carbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 14.2 g of 4-(11-cyanoundecanoyl)-1,2-dimethoxybenzene.

Aufarbeitung

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. washwashed successively with water, 5% aqueous sodium carbonate solution and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b6e028d988f245349ec49059757793a2
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05235068

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